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130693-82-2

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130693-82-2 Usage

Description

Different sources of media describe the Description of 130693-82-2 differently. You can refer to the following data:
1. Dorzolamide hydrochloride was introduced in the U.S.A. as eye drops for the treatment of open-angle glaucoma and ocular hypertension. Dorzolamide is a potent carbonic anhydrase inhibitor that, on topical administration, lowers intraocular pressure (IOP). In a clinical study in patients with bilateral primary open-angle glaucoma or ocular hypertension, dorzolamide (0.7-2%) was found to significantly lower IOP throughout the day. Dorzolamide has been shown to be effective as a single therapy or in combination with β-blockers.
2. Dorzolamide (hydrochloride) (Item No. 26303) is an analytical reference standard categorized as a carbonic anhydrase inhibitor diuretic. Diuretics have been used in sports doping to reduce weight or anabolic androgenic steroid-induced water retention, or as masking agents. This product is intended for use in analytical forensic applications. This product is also available as a general research tool .

Chemical Properties

White Powder

Originator

Merck (U.S.A.)

Uses

Different sources of media describe the Uses of 130693-82-2 differently. You can refer to the following data:
1. Carbonic anhydrase inhibitor. Antiglaucoma agent.
2. Antiglaucoma drug;Carbonic anhydrase inhibitor
3. analgesic
4. Dorzolamide HCl Ophthalmic Solution is indicated in the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma.
5. An inhibitor of carbonic anhydrase.

Definition

ChEBI: The hydrochloride salt of dorzolamide. It is used in ophthalmic solutions to lower increased intraocular pressure in the treatment of open-angle glaucoma and ocular hypertension.

Manufacturing Process

Manufacturing process for Dorzolamide hydrochloride includes these steps as follows: Step A: Sulfuric Acid Ritter Procedure;Step B: Sulfonylation Procedure Step C: Chlorosulfonylation Procedure;Step D: Amidation Procedure;Step E: Reduction via Borane Generated in situ Procedure;Step F: Maleate Salt Formation Procedure;Step G: Crude Hydrochloride Salt Formation;Step H: Recrystallization Procedure.

Therapeutic Function

Antiglaucoma

Veterinary Drugs and Treatments

Dorzolamide is often used in the contralateral eye of a dog with primary glaucoma to prevent development of bilateral disease. It is also an excellent agent to consider for most secondary glaucomas in dogs and cats because it has no effect on pupil size. Like the related oral carbonic anhydrase inhibitors (dichlorphenamide or Daranide?, methazolamide or Neptazane?), dorzolamide decreases aqueous humor production by the ciliary body epithelium by altering pH and affecting the H+/Na+ active transport exchange mechanism. Oral carbonic anhydrase inhibitors cause numerous systemic side effects such as metabolic acidosis and panting, diarrhea, vomiting, anorexia and others, all of which can be avoided with topical carbonic anhydrase inhibitors.

Check Digit Verification of cas no

The CAS Registry Mumber 130693-82-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,0,6,9 and 3 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 130693-82:
(8*1)+(7*3)+(6*0)+(5*6)+(4*9)+(3*3)+(2*8)+(1*2)=122
122 % 10 = 2
So 130693-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H16N2O4S3.ClH/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16;/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16);1H/t6-,8-;/m0./s1

130693-82-2 Well-known Company Product Price

  • Brand
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  • TCI America

  • (D4189)  Dorzolamide Hydrochloride  >98.0%(HPLC)(T)

  • 130693-82-2

  • 200mg

  • 990.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000726)  Dorzolamide hydrochloride  European Pharmacopoeia (EP) Reference Standard

  • 130693-82-2

  • Y0000726

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000750)  Dorzolamide for system suitability  European Pharmacopoeia (EP) Reference Standard

  • 130693-82-2

  • Y0000750

  • 1,880.19CNY

  • Detail

130693-82-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name dorzolamide hydrochloride

1.2 Other means of identification

Product number -
Other names Dorzolamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:130693-82-2 SDS

130693-82-2Synthetic route

(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt
1227941-29-8

(4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Stage #1: (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt With sodium hydrogencarbonate In water; ethyl acetate at 25 - 30℃; for 0.25h;
Stage #2: With hydrogenchloride In ethyl acetate; isopropyl alcohol at 25 - 85℃; for 12.5h; Product distribution / selectivity;
100%
With hydrogenchloride In isopropyl alcohol at 80℃; for 0.0833333 - 0.166667h; pH=3 - 4; Product distribution / selectivity; Heating / reflux;
Stage #1: (4S,6S)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno-[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide di-p-toluyl-L-tartate salt With sodium hydrogencarbonate In ethyl acetate at 20℃;
Stage #2: With hydrogenchloride In methanol; isopropyl alcohol for 0.666667h;
5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt

5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt With hydrogenchloride; sodium hydroxide In water at 52℃; pH=7.7; Inert atmosphere;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 75℃;
99.2%
Stage #1: 5,6-dihydro-(S)-4-(ethylamino)-(S)-6-methyl-4H-thieno<2,3-b>thiopyran-2-sulfonamide 7,7-dioxide maleate salt With sodium hydroxide In water at 52℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 75℃;
8.1 g
dorzolamide
120279-96-1

dorzolamide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethyl acetate pH=1;95%
With hydrogenchloride In water; dimethyl sulfoxide at 5 - 10℃; for 3h; pH=1.0;
5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride

5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Stage #1: 5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride With sulfuric acid; sulfur trioxide at 20℃; for 2 - 3h;
Stage #2: With thionyl chloride for 3 - 6h; Heating / reflux;
Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;
70%
Stage #1: 5,6-dihydro-4-(S)-ethylamino-6-(S)-methyl-4H-thieno[2,3-b]thiopyran-7,7-dioxide hydrochloride With sulfuric acid; sulfur trioxide at -7 - 20℃; for 22h;
Stage #2: With thionyl chloride at 20 - 65℃; for 24h;
Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages;
Reaxys ID: 11712783

Reaxys ID: 11712783

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
With (-)-di-p-toluoyl-L-tartaric acid22.48%
trans-5,6-dihydro-4-ethylamino-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

trans-5,6-dihydro-4-ethylamino-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Stage #1: trans-5,6-dihydro-4-ethylamino-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide; Di-p-toluoyl-L-tartaric acid In propan-1-ol Heating / reflux;
Stage #2: With sodium hydrogencarbonate In water
Stage #3: With hydrogenchloride In ethanol
22.48%
2C10H16N2O4S3*C11H10O7

2C10H16N2O4S3*C11H10O7

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Stage #1: 2C10H16N2O4S3*C11H10O7 With sodium carbonate In water; ethyl acetate
Stage #2: With hydrogenchloride In ethyl acetate; isopropyl alcohol pH=1 - 2;
5,6-dihydro-6-methyl-4-oxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

5,6-dihydro-6-methyl-4-oxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: dihydrogen peroxide / sodium tungstate (VI) dihydrate / ethyl acetate; water / -20 °C
2.1: water; sodium tetrahydroborate; methanol / ethyl acetate / 10 - 20 °C
3.1: sulfuric acid / 0 - 30 °C
3.2: 10 °C / pH 7 - 8
4.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C
4.2: 5 - 20 °C
5.1: sodium hydroxide / 20 °C / pH 7.5 - 8
6.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
7.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
7.2: 0.67 h
View Scheme
4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

4-hydroxy-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sulfuric acid / 0 - 30 °C
1.2: 10 °C / pH 7 - 8
2.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C
2.2: 5 - 20 °C
3.1: sodium hydroxide / 20 °C / pH 7.5 - 8
4.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
5.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
5.2: 0.67 h
View Scheme
(+/-)-(4S,6S;4R,6R)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

(+/-)-(4S,6S;4R,6R)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
2.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
2.2: 0.67 h
View Scheme
(+/-)-(4S,6S;4R,6R)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide maleate

(+/-)-(4S,6S;4R,6R)-4-(ethylamino)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide maleate

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / 20 °C / pH 7.5 - 8
2.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
3.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
3.2: 0.67 h
View Scheme
N-(6-methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide

N-(6-methyl-7,7-dioxido-2-sulfamoyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-yl)acetamide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C
1.2: 5 - 20 °C
2.1: sodium hydroxide / 20 °C / pH 7.5 - 8
3.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
4.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
4.2: 0.67 h
View Scheme
6-methyl-4-oxo-5,6-dihydro-4H-thieno[2.3-b]thiopyran-2-sulfonamide-7,7-dioxide
935289-26-2

6-methyl-4-oxo-5,6-dihydro-4H-thieno[2.3-b]thiopyran-2-sulfonamide-7,7-dioxide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: water; sodium tetrahydroborate; methanol / ethyl acetate / 10 - 20 °C
2.1: sulfuric acid / 0 - 30 °C
2.2: 10 °C / pH 7 - 8
3.1: sodium tetrahydroborate / tetrahydrofuran / -5 - 5 °C
3.2: 5 - 20 °C
4.1: sodium hydroxide / 20 °C / pH 7.5 - 8
5.1: isopropyl alcohol; acetonitrile / 1 h / 70 °C / Reflux
6.1: sodium hydrogencarbonate / ethyl acetate / 20 °C
6.2: 0.67 h
View Scheme
(6S)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide
1383784-43-7

(6S)-5,6-dihydro-6-methyl-4H-thieno[2,3-b]thiopyran-4-one-2-sulfonamide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium tungstate (VI) dihydrate; oxygen / methanol; water / 6 h / 10 - 50 °C / Inert atmosphere
2.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 15 °C / Inert atmosphere
3.1: methanesulfonic acid / 18 h / 10 - 87 °C / Inert atmosphere
3.2: 4.5 h / 7 - 40 °C / pH 7.3
4.1: borane-THF / tetrahydrofuran / 17 h / 38 °C / Inert atmosphere
4.2: 40 °C
5.1: sodium hydroxide / water / 52 °C / Inert atmosphere
5.2: 75 °C
View Scheme
(6S)-4-oxo-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide
154716-03-7

(6S)-4-oxo-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 15 °C / Inert atmosphere
2.1: methanesulfonic acid / 18 h / 10 - 87 °C / Inert atmosphere
2.2: 4.5 h / 7 - 40 °C / pH 7.3
3.1: borane-THF / tetrahydrofuran / 17 h / 38 °C / Inert atmosphere
3.2: 40 °C
4.1: sodium hydroxide / water / 52 °C / Inert atmosphere
4.2: 75 °C
View Scheme
cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

cis-(6S)-4-hydroxy-5,6-dihydro-6-methyl-7,7-dioxo-4H-thieno[2,3-b]thiopyran-2-sulfonamide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanesulfonic acid / 18 h / 10 - 87 °C / Inert atmosphere
1.2: 4.5 h / 7 - 40 °C / pH 7.3
2.1: borane-THF / tetrahydrofuran / 17 h / 38 °C / Inert atmosphere
2.2: 40 °C
3.1: sodium hydroxide / water / 52 °C / Inert atmosphere
3.2: 75 °C
View Scheme
(4S,6S)‑4‑acetamido‑5,6‑dihydro‑6‑methyl‑4H‑thieno[2,3‑b]thiopyran‑2‑sulfonamide‑7,7‑dioxide
147200-03-1

(4S,6S)‑4‑acetamido‑5,6‑dihydro‑6‑methyl‑4H‑thieno[2,3‑b]thiopyran‑2‑sulfonamide‑7,7‑dioxide

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: borane-THF / tetrahydrofuran / 17 h / 38 °C / Inert atmosphere
1.2: 40 °C
2.1: sodium hydroxide / water / 52 °C / Inert atmosphere
2.2: 75 °C
View Scheme
(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one
147086-79-1

(S)-5,6-dihydro-6-methylthieno<2,3-b>thiopyran-4-one

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: thionyl chloride; chlorosulfonic acid / 10 h / -3 - 28 °C / Inert atmosphere
2.1: ammonia / methanol; acetone / -10 °C / Inert atmosphere
3.1: sodium tungstate (VI) dihydrate; oxygen / methanol; water / 6 h / 10 - 50 °C / Inert atmosphere
4.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 15 °C / Inert atmosphere
5.1: methanesulfonic acid / 18 h / 10 - 87 °C / Inert atmosphere
5.2: 4.5 h / 7 - 40 °C / pH 7.3
6.1: borane-THF / tetrahydrofuran / 17 h / 38 °C / Inert atmosphere
6.2: 40 °C
7.1: sodium hydroxide / water / 52 °C / Inert atmosphere
7.2: 75 °C
View Scheme
(S)-6-methyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonyl chloride
1083006-59-0

(S)-6-methyl-4-oxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonyl chloride

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: ammonia / methanol; acetone / -10 °C / Inert atmosphere
2.1: sodium tungstate (VI) dihydrate; oxygen / methanol; water / 6 h / 10 - 50 °C / Inert atmosphere
3.1: sodium tetrahydroborate / water; tetrahydrofuran / 2 h / 15 °C / Inert atmosphere
4.1: methanesulfonic acid / 18 h / 10 - 87 °C / Inert atmosphere
4.2: 4.5 h / 7 - 40 °C / pH 7.3
5.1: borane-THF / tetrahydrofuran / 17 h / 38 °C / Inert atmosphere
5.2: 40 °C
6.1: sodium hydroxide / water / 52 °C / Inert atmosphere
6.2: 75 °C
View Scheme
(6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

(6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide

A

4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride
1417607-96-5

4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride

B

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In acetone at 0 - 5℃; for 2h; pH=1 - 2;A n/a
B n/a
(6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride

(6S)-4-(ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide hydrochloride

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

Conditions
ConditionsYield
In methanol; water for 2h; Solvent; Reflux;3.2 g
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

(E)-N'-{[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}-N,N-dimethylmethanimidamide

(E)-N'-{[(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ6-thieno[2,3-b]thiopyran-6-yl]sulfonyl}-N,N-dimethylmethanimidamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;80%
1,8-octanediol bis(4-nitrophenylcarbonate)

1,8-octanediol bis(4-nitrophenylcarbonate)

dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

8-(((((4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxido-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-yl)sulfonyl)carbamoyl)oxy)octyl (((4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxido-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-yl)sulfonyl)carbamate

8-(((((4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxido-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-yl)sulfonyl)carbamoyl)oxy)octyl (((4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxido-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-yl)sulfonyl)carbamate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;56%
dorzolamide hydrochloride
130693-82-2

dorzolamide hydrochloride

N,N-dimethylformamide diethyl diacetal
1188-33-6

N,N-dimethylformamide diethyl diacetal

N'-[(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-2-sulfonyl]-N,N-dimethylmethanimidamide
1034583-83-9

N'-[(4S,6S)-4-(ethylamino)-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7λ6-thieno[2,3-b]thiopyran-2-sulfonyl]-N,N-dimethylmethanimidamide

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;

130693-82-2Downstream Products

130693-82-2Relevant articles and documents

Chiral synthesis method of dorzolamide hydrochloride

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Paragraph 0023-0027, (2021/09/04)

The invention relates to a chiral synthesis method of dorzolamide hydrochloride, which comprises the following steps: (1) by taking a compound I that is (6S)-4-carbonyl-5,6-dihydro-4H-6-methyl-thieno[2,3b] thiopyran-2-sulfonamide-7,7-dioxide as an initial raw material, carrying out imidization reaction on the initial raw material and ethylamine to obtain a compound II that is (6S)-4-ethyl imino-5,6-dihydro-4H-6-methyl-thieno[2, 3b]thiopyran-2-sulfonamide-7,7-dioxide; (2) carrying out asymmetric hydrogenation reaction on the compound II obtained in the step (1), a catalyst and a chiral ligand (R)-(+)-1,1'-binaphthyl-2'-isopropoxy-2-diphenylphosphine to obtain a compound III that is dorzolamide; and (3) mixing the compound III obtained in the step (2) with hydrochloric acid, acidifying, washing and drying to obtain a compound IV, namely dorzolamide hydrochloride. The synthesis method is simple and easy to implement, high in chiral selectivity and low in cost, and the obtained dorzolamide hydrochloride is high in purity and suitable for industrial production.

PROCESS FOR THE PREPARATION OF DORAOLZMIDE HYDROCHLORIDE

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Page/Page column 13, (2018/04/21)

The present invention discloses an improved process for the preparation of dorzolamide hydrochloride the compound of Formula I.

PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED OXAMIDES

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Page/Page column 15; 16, (2014/01/18)

The present invention relates to a chiral oxamide of formula (I) useful as an intermediate in the preparation of dorzolamide, and to the preparation thereof. The invention also relates to the preparation of dorzolamide, to the hydrochloride salt thereof, and to the active ingredient contained in a drug useful in the treatment of glaucoma, by means of the intermediate of formula (I).

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