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

HRID 1266873Notes

Reaction equation

HRID 1266873 reaction equation
[CH2:1]([O:3][C:4]1[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][C:7]2[NH:8][C:9](=[O:26])[CH2:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N:19]4[C:23]([CH2:24]O)=[CH:22][N:21]=[N:20]4)[CH:14]=3)=[N:12][C:6]=2[CH:5]=1)[CH3:2].O=S(Cl)Cl.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[CH:37]1([NH:40][CH2:24][C:23]2[N:19]([C:15]3[CH:14]=[C:13]([C:11]4[CH2:10][C:9](=[O:26])[NH:8][C:7]5[CH:27]=[C:28]([C:29]([F:30])([F:31])[F:32])[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]=5[N:12]=4)[CH:18]=[CH:17][CH:16]=3)[N:20]=[N:21][CH:22]=2)[CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 18548850HCID 18548850, compound

Product 1

HCID 185487164-[3-(5-Cyclopropylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-7-ethoxy-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Procedure

The title compound was prepared from 7-ethoxy-4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 52) (134 mg, 0.3 mmol) by treatment with SOCl2 (3 eq.) and cyclopropylamine (10 eq.) as described in Example 47. Obtained as a yellow solid (55 mg).

Sources & evidence

ORD record
ord-0b2d066814084caca9cc640f343f7716
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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