67863-05-2

Basic information

• Product Name: N-Isopropylglycinamide
• Synonyms: propan-2-ylcarbamoylmethylazanium;N-Isopropylglycinamide;2-Amino-N-isopropylacetamide;N~1~-isopropylglycinamide(SALTDATA: HCl)
• CAS NO: 67863-05-2
• Molecular Formula: C₅H₁₂N₂O
• Molecular Weight: 116.16
• EINECS: 1312995-182-4
• Mol File: 67863-05-2.mol

Chemical Properties

• Melting Point: 68 °C
• Boiling Point: 260.2 °C at 760 mmHg
• Flash Point: 111.2 °C
• Appearance: /
• Density: 0.959 g/cm³
• Vapor Pressure: 0.0124mmHg at 25°C
• PKA: 15.07±0.46(Predicted)
• CAS DataBase Reference: N-Isopropylglycinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropylglycinamide(67863-05-2)
• EPA Substance Registry System: N-Isopropylglycinamide(67863-05-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 67863-05-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Isopropylglycinamide is used as a building block for the synthesis of vasopressin-V1b receptor antagonists. These antagonists are important in the development of drugs targeting various medical conditions, such as stress-related disorders and certain types of hypertension. N-Isopropylglycinamide's structure allows for the creation of molecules that can specifically bind to and block the V1b receptor, thus modulating the effects of vasopressin in the body.
Additionally, N-Isopropylglycinamide is used as a peptidomimetic inhibitor of serine proteases with trypsin properties. Serine proteases are a class of enzymes that play crucial roles in various biological processes, including blood clotting, immune response, and digestion. Inhibitors of these enzymes can be used to regulate their activity, which may be beneficial in treating conditions related to uncontrolled proteolysis, such as certain inflammatory diseases and cancer.

InChI:InChI=1/C5H12N2O/c1-4(2)7-5(8)3-6/h4H,3,6H2,1-2H3,(H,7,8)/p+1

Upstream product

• 78639-46-0 (isopropylcarbamoylmethyl)carbamic acid benzyl ester 
• 158976-14-8 Boc-Gly-NHC₃H₇ 

Downstream Products

• 1011029-44-9 (E)-2-[2-(4-fluoro-3-methoxyphenyl)vinyl]-5-(4-methoxybenzyloxy)benzoic acid 4-methoxybenzyl ester 
• 1011029-57-4 2-[3-(3-chlorophenyl)-7-methoxy-1-oxo-1H-isoquinolin-2-yl]-N-isopropylacetamide 
• 909391-39-5 2-amino-5-hydroxy-N-(isopropylcarbamoylmethyl)benzamide 
• 909391-53-3 5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide 
• 1314039-73-0 C₂₉H₃₀N₄O₂ 
• 1314039-76-3 C₃₀H₃₂N₄O₃ 
• 909392-66-1 2-[6-bromo-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide 
• 909392-65-0 N-isopropyl-2-[2-(3-methoxyphenyl)-4-oxo-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-4H-quinazolin-3-yl]acetamide 
• 909393-04-0 C₂₆H₂₄N₄O₄ 
• 909393-03-9 2-[6-(5-formylfuran-2-yl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-isopropylacetamide 

Relevant articles and documents

Acryloyl-N-isopropylglycinamide monomer and preparation method thereof

The invention discloses an acryloyl-N-isopropylglycinamide monomer and a preparation method thereof. Specifically, N-(tert-butoxycarbonyl) glycine methyl ester, isopropylamine and acryloyl chloride are used as raw materials and react under a certain condition to generate acryloyl-N-isopropylglycinamide. The acryloyl-N-isopropylglycinamide has double bonds and can be subjected to free radical polymerization. Meanwhile, acryloyl-N-isopropylglycinamide has hydrophobic isopropyl and two hydrophilic amide groups, and the hydrophilic amide groups can provide a double hydrogen bond structure. Isopropyl can endow polymer molecules with temperature characteristic similar to that of poly (N-isopropylacrylamide), and the double hydrogen bond structure enables multiple hydrogen bond effects to be achieved between polymer molecules and in molecules. Therefore, the monomer can be polymerized to form a polymer, so that a polymer material with special temperature sensitivity is obtained, and the polymer material has potential application value in the field of bioengineering.

Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)?H arylation

Glycinamide hydrochloride as an inexpensive and commercially available transient directing group for the C(sp3)?H arylation of 2-methylbenzaldehydes is described. A series of practical 2-benzylbenzaldehydes bearing various functional groups are efficiently synthesized in satisfactory yield by this strategy. This method can also be extended to gram scale.

Palladium-catalyzed β-C-H arylation of aliphatic aldehydes and ketones using amino amide as a transient directing group

This paper describes a new amino-amide-based transient directing group (TDG). The TDG can exhibit better performance in the Pd-catalyzed arylation of aliphatic aldehydes and ketones. This reaction showed good substrate compatibility and regioselectivity. The results indicated that 3-amino-N-isopropylpropionamide was more beneficial to the β-arylation of aliphatic aldehydes than other TDGs under relatively mild conditions.

Palladium-Catalyzed β-C?H Arylation of Ketones Using Amino Amide as a Transient Directing Group: Applications to Synthesis of Phenanthridinone Alkaloids

The direct arylation of aromatic and aliphatic ketones was carried out via palladium-catalyzed inert C?H bond functionalization with 2-amino-N-isopropyl-acetamide as a new catalytic transient directing group. The reaction showed excellent functional group compatibility and site selectivity. We demonstrated that α-amino amide forming N,N-bidentate coordination with Pd catalyst is more favorable for the β-arylation of ketones than α-amino acid forming N,O-bidentate coordination with Pd catalyst under relatively mild conditions. This elegant approach provides straightforward access to important structural motifs in organic and medicinal chemistry and is demonstrated here in the efficient synthesis of phenanthridinone alkaloids. (Figure presented.).

Oligomeric epoxide-amine adducts based on 2-amino-N-isopropylacetamide and a-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

2-Amino-N-isopropylacetamide and α-amino-ε-caprolactam were reacted with glycerol diglycidyl ether to give novel oligomeric thermoresponsive epoxide-amine adducts. These oligomers exhibit a lower critical solution temperature (LCST) behavior in water. The solubility properties were influenced with randomly methylated β-cyclodextrin (RAMEB-CD) and the curing properties of the amine-epoxide mixtures were analyzed by oscillatory rheology and differential scanning calorimetry, whereby significant differences in setting time, viscosity, and stiffness were observed.

Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines

The benzamidine moiety, a well-known arginine mimetic, has been introduced in a variety of ligands, including peptidomimetic inhibitors of trypsin-like serine proteases. According to their primary substrate specificity, the benzamidine residue interacts with the negatively charged aspartate at the bottom of the S1 pocket of such enzymes. Six series of benzamidine derivatives (1-73) were synthesized and evaluated as inhibitors of two prototype serine proteases, that is, bovine trypsin and human thrombin. As a further target, human matriptase-2, a recently discovered type II transmembrane serine protease, was investigated. Matriptase-2 represents an important regulatory protease in iron homeostasis by down-regulation of the hepcidin expression. Compounds 1-73 were designed to contain a fixed sulfamoyl benzamidine moiety as arginine mimetic and a linker-connected additional substructure, such as a tert-butyl ester, carboxylate or second benzamidine functionality. A systematic mapping approach was performed with these inhibitors to scan the active site of the three target proteases. In particular, bisbenzamidines, able to interact with both the S1 and S3/S4 binding sites, showed notable affinity. In branched bisbenzamidines 66-73 containing a third hydrophobic residue, opposite effects of the stereochemistry on trypsin and thrombin inhibition were observed.

2-(1-OXO-1H-ISOQUINOLIN-2-YL)ACETAMIDE DERIVATIVES

Disclosed herein are 2-(1-oxo-1H-isoquinolin-2-yl)acetamide derivative of formula I, or pharmaceutically acceptable salts or solvates thereof wherein each of the substituents is given the definition as set forth in the specification and claims. Also disclosed are pharmaceutical compositions comprising 2-(1-oxo-1H-isoquinolin-2-yl)acetamide derivatives according to the present invention and their use in therapy.

QUINAZOLINONE AND ISOQUINOLINONE ACETAMIDE DERIVATIVES

The present invention relates to a quinazolinone or isoquinolinone derivative of formula I, wherein R1 is C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkylC1-3alkyl, C2-6alkenyl, C2-6alkynyl, said C1-6alkyl, C3-6cycloalkyl and C3-6cycloalkylC1-3alkyl being optionally substituted with hydroxy, C1-6alkyloxy, cyano or one or more halogens; R2 is C6-10aryl optionally substituted with one to three substituents selected from halogen, hydroxy, cyano, C1-6alkyl, C3-6cycloalkyl, C1-6alkyloxy and C3-6cycloalkyloxy, said C1-6alkyl, C3-6 cycloalkyl, C1-6 alkyloxy and C3-6Cycloalkyloxy being optionally substituted with one or more halogens; or R2 is a 5-10 membered heteroaryl ring system comprising a heteroatom selected from N, O and S and optionally substituted with a substituent selected from methyl, C1-6alkyloxy and halogen; or R2 is C4-7cycloalkyl; R3 is an optional substituent selected from C1-6alkyl, C1-6alkyloxy and halogen, said C1-6alkyl and C1-6alkyloxy being optionally substituted with one or more halogens; R4 is a group located at the 6- or 7- position of the quinazolinone or isoquinolinone ring having the formula Il, wherein R5 together with one of R6 forms a 4-8 membered saturated or unsaturated heterocyclic ring optionally comprising a further heteroatomic moiety selected from O, S and NR9, said heterocyclic ring being optionally substituted with one or two substituents selected from methyl, halogen, hydroxy and oxo or R5 together with one of R7 and R8 forms a 6-8 membered heterocyclic ring optionally substituted with one or two substituents selected from methyl, halogen, hydroxy and oxo; Each R6 is independently H, halogen or C1-4alkyl optionally substituted with halogen or SO2CH3 or one of R6 together with R5 forms a 4-8 membered saturated or unsaturated heterocyclic ring optionally comprising a further heteroatomic moiety selected from O, S and NR9, said heterocyclic ring being optionally substituted with one or two substituents selected from methyl, halogen, hydroxy and oxo; R7 and R8 are independently H, C1-6alkyl, C3-6cycloalkyl, C3-6cycloalkylc1-3alkyl, cyanoC1-3alkyl, C6-10aryl, C6-10arylC1-3alkyl, C1-3alkyloxyC1-3alkyl or C1-6acyl said C1-6alkyl, C3-6cycloalkyl and C3-6cycloalkylC1-3alkyl being optionally substituted with hydroxy, 1 or more halogens or diC1-2alkylamino; or R7 and R8 together with the nitrogen to which they are bonded form a 4-8 membered saturated or unsaturated heterocyclic ring optionally comprising a further heteroatomic moiety selected from O, S and NR10, said heterocyclic ring being optionally substituted with one or two substituents selected from C1-6alkyl, halogen, hydroxy,

2- (4-0X0-4H-QUINAZ0LIN-3-YL) ACETAMIDES AND THEIR USE AS VASOPRESSIN V3 ANTAGONISTS

The present invention relates to 2-(4-oxo4H-quinazolin-3-yl)acetamicle derivatives of formula (I), and to their use as vasopressin V3 antagonists, particularly for the treatment of depression.