Thionyl Chloride → 4-[3-(5-Cyclopropylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-7-dimethylamino-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265825Notes

Reaction equation

[CH3:1][N:2]([CH3:32])[C:3]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][C:6]2[NH:7][C:8](=[O:25])[CH2:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N:18]4[C:22]([CH2:23]O)=[CH:21][N:20]=[N:19]4)[CH:13]=3)=[N:11][C:5]=2[CH:4]=1.O=S(Cl)Cl.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[CH:37]1([NH:40][CH2:23][C:22]2[N:18]([C:14]3[CH:13]=[C:12]([C:10]4[CH2:9][C:8](=[O:25])[NH:7][C:6]5[CH:26]=[C:27]([C:28]([F:29])([F:31])[F:30])[C:3]([N:2]([CH3:32])[CH3:1])=[CH:4][C:5]=5[N:11]=4)[CH:17]=[CH:16][CH:15]=3)[N:19]=[N:20][CH:21]=2)[CH2:39][CH2:38]1

Participants

Reactant 3

HCID 24386Thionyl Chloride

HCID 69828Cyclopropylamine

HCID 186133777-Dimethylamino-4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 186131304-[3-(5-Cyclopropylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-7-dimethylamino-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Procedure

The title compound was prepared from 7-dimethylamino-4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 17) (444 mg, 1.0 mmol) by treatment with SOCl2 (3 eq.) and cyclopropyl amine (10 eq.) as described in Example 45. Obtained as a yellow solid (248 mg).

Sources & evidence

ORD record: ord-bbdad9d4a8ae44f183593c3c6c20e5ce
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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