Cyclopropanecarboxylic acid, 1-amino-, hydrochloride (1:1) → Racemic (1S,2R)-5'-(4-chlorophenyl)-2,6',7'-trimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

HRID 1772354Notes

Reaction equation

HRID 1772354 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3C(C)=NN=C3C(C)(C)N=2)=[CH:4][CH:3]=1.Cl.[NH2:27][C:28]1([C:32]([O:34]CC)=O)[CH2:30][CH:29]1[CH3:31].Cl.NC1(C(O)=O)CC1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[NH:12][C:32](=[O:34])[C:28]3([CH2:30][CH:29]3[CH3:31])[N:27]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 11957445Cyclopropanecarboxylic acid, 1-amino-, hydrochloride (1:1)HCID 545887644-(4-chlorophenyl)-2,3,6,6,9-pentamethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepineHCID 131734666racemic (1S,2R)-ethyl 1-amino-2-methylcyclopropanecarboxylate hydrochloride

Product 1

HCID 137119440Racemic (1S,2R)-5'-(4-chlorophenyl)-2,6',7'-trimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

Procedure

A procedure analogous to that set forth in the synthesis of Compound 214 was followed, with the exception that racemic (1S,2R)-ethyl 1-amino-2-methylcyclopropanecarboxylate hydrochloride was used as starting material instead of 1-aminocyclopropanecarboxylate hydrochloride. LRMS (M+H)+: 345 m/z.

Sources & evidence

ORD record
ord-766ba38530314b14b1d85bfa1084d39e
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

Loading…