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159634-47-6

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159634-47-6 Usage

Description

Ibutamoren (INN) (developmental code names MK-677, MK-0677, L-163,191)is a non-peptidic, potent, long acting, orally-active, and selective agonist of the ghrelin receptor and a growth hormone secretagogue, mimicking the growth hormone (GH)-stimulating action of the endogenous hormone ghrelin. It has been demonstrated to increase the release of, and produces sustained increases in plasma levels of several hormones including GH and insulin-like growth factor 1 (IGF-1), but without affecting cortisol levels. MK677 has shown to sustain activation of GH-IGF-1 Axis and increase in lean body mass but no change in total fat mass or visceral fat. It is currently under development as a potential treatment for reduced levels of these hormones, such as in children or elderly adults with growth hormone deficiency, and human studies have shown it to increase both muscle mass and bone mineral density, making it a promising therapy for the treatment of frailty in the elderly.

Uses

Growth hormone releasing factor.

Safety

Ibutamoren is a muscle building anabolic compound. It's considered safe if you don't have high blood glucose level and if you don't suffer from congestive heart failure. It's considered a boon for anti aging and it's a life longevity material. It's considered to be more beneficial than to be harmful. The optimal dose for body building is to take 25mg at bedtime for four to six weeks. It is a water retaining compound so beware of bloating.

Check Digit Verification of cas no

The CAS Registry Mumber 159634-47-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,9,6,3 and 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 159634-47:
(8*1)+(7*5)+(6*9)+(5*6)+(4*3)+(3*4)+(2*4)+(1*7)=166
166 % 10 = 6
So 159634-47-6 is a valid CAS Registry Number.
InChI:InChI=1/C27H36N4O5S/c1-26(2,28)25(33)29-22(18-36-17-20-9-5-4-6-10-20)24(32)30-15-13-27(14-16-30)19-31(37(3,34)35)23-12-8-7-11-21(23)27/h4-12,22H,13-19,28H2,1-3H3,(H,29,33)/t22-/m1/s1

159634-47-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-amino-2-methyl-N-[(2R)-1-(1-methylsulfonylspiro[2H-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamide

1.2 Other means of identification

Product number -
Other names MK-0667

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:159634-47-6 SDS

159634-47-6Synthetic route

N-[(R)-[(1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperidin]-1'-yl)carbonyl]-2-(phenylmethyloxy)ethyl]-2-[(1,1-dimethyl-ethoxy)carbonyl]amino-2-methyl-propanamide
159634-87-4

N-[(R)-[(1,2-Dihydro-1-methanesulfonylspiro[3H-indole-3,4'-piperidin]-1'-yl)carbonyl]-2-(phenylmethyloxy)ethyl]-2-[(1,1-dimethyl-ethoxy)carbonyl]amino-2-methyl-propanamide

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
With methanesulfonic acid In ethanol at 35 - 40℃; Yield given;
isonipecotic acid
498-94-2

isonipecotic acid

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 97 percent / K2CO3 / H2O / 58 h / 22 °C
2: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C
3: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
4: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
5: NaBH4 / toluene / 0.5 h / -2 °C
6: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
7: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
8: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
9: MsOH / ethanol / 7.5 h / 35 - 40 °C
10: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
11: MsOH / ethanol / 35 - 40 °C
View Scheme
N-Boc-D-serine(Bzl)-OH
47173-80-8

N-Boc-D-serine(Bzl)-OH

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
2: MsOH / ethanol / 7.5 h / 35 - 40 °C
3: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
4: MsOH / ethanol / 35 - 40 °C
View Scheme
benzyl bromide
100-39-0

benzyl bromide

potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide>

potassium-compound of propionic acid-<1-methyl-2-oxo-propylidenehydrazide>

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 74 percent / NaOt-Am / dimethylformamide / 1 h / -10 °C
2: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
3: MsOH / ethanol / 7.5 h / 35 - 40 °C
4: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
5: MsOH / ethanol / 35 - 40 °C
View Scheme
1-benzyloxycarbonylpiperidine-4-carboxylic acid
10314-98-4

1-benzyloxycarbonylpiperidine-4-carboxylic acid

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: (COCl)2 / toluene; dimethylformamide / 16 h / 18 °C
2: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
3: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
4: NaBH4 / toluene / 0.5 h / -2 °C
5: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
6: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
7: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
8: MsOH / ethanol / 7.5 h / 35 - 40 °C
9: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
10: MsOH / ethanol / 35 - 40 °C
View Scheme
N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde
138163-08-3

N-(benzyloxycarbonyl)piperidine-4-carboxaldehyde

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
2: NaBH4 / toluene / 0.5 h / -2 °C
3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
4: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
5: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
6: MsOH / ethanol / 7.5 h / 35 - 40 °C
7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
8: MsOH / ethanol / 35 - 40 °C
View Scheme
benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate
10314-99-5

benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 94 percent / H2, DIEA, thioanisole / Pd/C / toluene / 22 h / 20 °C / 2068.6 Torr
2: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
3: NaBH4 / toluene / 0.5 h / -2 °C
4: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
5: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
6: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
7: MsOH / ethanol / 7.5 h / 35 - 40 °C
8: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
9: MsOH / ethanol / 35 - 40 °C
View Scheme
phenylhydrazine
100-63-0

phenylhydrazine

1.4-diphenyl-butanedione-(2.3)

1.4-diphenyl-butanedione-(2.3)

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 99 percent / TFA / CH2Cl2 / 17 h / 35 °C
2: NaBH4 / toluene / 0.5 h / -2 °C
3: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
4: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
5: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
6: MsOH / ethanol / 7.5 h / 35 - 40 °C
7: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
8: MsOH / ethanol / 35 - 40 °C
View Scheme
1-(methylsulfonyl)spiro[indoline-3,4’-piperidine]
178261-41-1

1-(methylsulfonyl)spiro[indoline-3,4’-piperidine]

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
2: MsOH / ethanol / 7.5 h / 35 - 40 °C
3: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
4: MsOH / ethanol / 35 - 40 °C
View Scheme
benzyl spiro[indole-3,4'-piperidine]-1'-carboxylate
184289-85-8

benzyl spiro[indole-3,4'-piperidine]-1'-carboxylate

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: NaBH4 / toluene / 0.5 h / -2 °C
2: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
3: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
4: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
5: MsOH / ethanol / 7.5 h / 35 - 40 °C
6: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
7: MsOH / ethanol / 35 - 40 °C
View Scheme
benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate
167484-18-6

benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: DIEA / tetrahydrofuran / 2 h / 5 - 8 °C
2: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
3: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
4: MsOH / ethanol / 7.5 h / 35 - 40 °C
5: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
6: MsOH / ethanol / 35 - 40 °C
View Scheme
benzyl 1-(methylsulfonyl)spiro[indoline-3,4’-piperidine]-1‘-carboxylate
184289-84-7

benzyl 1-(methylsulfonyl)spiro[indoline-3,4’-piperidine]-1‘-carboxylate

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 93 percent / H2 / Pd-C / ethanol / 5 h / 65 °C / 2068.6 Torr
2: DCC, HOBt / H2O; various solvent(s) / 5 h / Ambient temperature
3: MsOH / ethanol / 7.5 h / 35 - 40 °C
4: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
5: MsOH / ethanol / 35 - 40 °C
View Scheme
C23H29N3O4S
180465-67-2

C23H29N3O4S

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
2: MsOH / ethanol / 35 - 40 °C
View Scheme
C28H37N3O6S
180465-66-1

C28H37N3O6S

Ibutamoren
159634-47-6

Ibutamoren

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: MsOH / ethanol / 7.5 h / 35 - 40 °C
2: DCC, HOBt / various solvent(s) / 2 h / Ambient temperature
3: MsOH / ethanol / 35 - 40 °C
View Scheme
methanesulfonic acid
75-75-2

methanesulfonic acid

Ibutamoren
159634-47-6

Ibutamoren

MK-677

MK-677

Conditions
ConditionsYield
In ethanol; ethyl acetate at 55℃; Yield given;

159634-47-6Downstream Products

159634-47-6Relevant articles and documents

Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

Maligres, Peter E.,Houpis, Ioannis,Rossen, Kai,Molina, Audrey,Sager, Jess,Upadhyay, Veena,Wells, Kenneth M.,Reamer, Robert A.,Lynch, Joseph E.,Askin, David,Volante,Reider, Paul J.,Houghton, Peter

, p. 10983 - 10992 (2007/10/03)

The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.

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