Ethyl 1-aminocyclopropane-1-carboxylate hydrochloride → 5'-(4-chlorophenyl)-6',7'-dimethylspiro[cyclopropane-1,3'-thieno[2,3-e][1,4]diazepin]-2'(1'H)-one

HRID 1772351Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([CH3:17])=[C:5]([CH3:16])[C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)=O.Cl.[NH2:19][C:20]1([C:23](OCC)=[O:24])[CH2:22][CH2:21]1>N1C=CC=CC=1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[C:6]3[C:5]([CH3:16])=[C:4]([CH3:17])[S:3][C:2]=3[NH:1][C:23](=[O:24])[C:20]3([CH2:22][CH2:21]3)[N:19]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A microwave vial was charged with (2-amino-4,5-dimethylthiophen-3-yl)(4-chlorophenyl)methanone (1.605 g, 6.04 mmol), ethyl 1-aminocyclo-propanecarboxylate hydrochloride (1 g, 6.04 mmol), and a stir bar. Pyridine (6 mL, 1.0 M) was added, and the mixture was stirred in the microwave at 120° C. for 24 h. The reaction mixture was purified by flash chromatography (hexane/EtOAc) and triturated from DMF with water to give 5′-(4-chlorophenyl)-6′,7′-dimethylspiro[cyclopropane-1,3′-thieno[2,3-e][1,4]diazepin]-2′(1′H)-one as a brown amorphous solid (354 mg). LRMS (M+H)+: 331 m/z.

Workup

customThe reaction mixture was purified by flash chromatography (hexane/EtOAc)
customtriturated from DMF with water

Sources & evidence

ORD record: ord-bb695b70277b460e98e10778882911f9
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249161B2

Reaction notes

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