Methyl 2-(1-aminocyclopropyl)acetate hydrochloride → 2-[1-[(8aR)-3-oxo-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyrazin-2yl]cyclopropyl]acetic acid

HRID 590565Notes

Reaction equation

HRID 590565 reaction equation
[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C@H:5]2[CH2:4][N:3]1[CH2:11][C:12](C)(C)[C:13]([OH:15])=[O:14].Cl.N[C:20]1(CC(OC)=O)C[CH2:21]1>>[O:1]=[C:2]1[N:6]2[CH2:7][CH2:8][NH:9][CH2:10][C@@H:5]2[CH2:4][N:3]1[C:11]1([CH2:12][C:13]([OH:15])=[O:14])[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 57350660Methyl 2-(1-aminocyclopropyl)acetate hydrochlorideHCID 118354187(S)-2,2-Dimethyl-3-(3-oxohexahydroimidazo[1,5-a]pyrazin-2(3H)-yl)propanoic acid

Product 1

HCID 1183541252-[1-[(8aR)-3-oxo-1,5,6,7,8,8a-hexahydroimidazo[1,5-a]pyrazin-2yl]cyclopropyl]acetic acid

Procedure

Compound 47-A was prepared in analogy to compound Q in Example 19 by using methyl 2-(1-aminocyclopropyl)acetate hydrochloride salt (for its synthesis, refer to: Sandstroem A., et al, Bioorganic & Medicinal Chemistry, 16(10), 5590-5605; 2008) instead of ethyl 3-amino-2,2-dimethyl-propanoate hydrochloride salt.

Sources & evidence

ORD record
ord-2dbaecbd2fba4669bc2354115d9f2d38
Source dataset
uspto-grants-2016_01
Patent number
US09233978B2

Reaction notes

Loading…