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

HRID 1265823Notes

Reaction equation

HRID 1265823 reaction equation
[CH:1]1([CH2:4][N:5]([CH3:35])[C:6]2[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][C:9]3[NH:10][C:11](=[O:28])[CH2:12][C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([N:21]5[C:25]([CH2:26]O)=[CH:24][N:23]=[N:22]5)[CH:16]=4)=[N:14][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.O=S(Cl)Cl.[CH:40]1([NH2:43])[CH2:42][CH2:41]1>>[CH:40]1([NH:43][CH2:26][C:25]2[N:21]([C:17]3[CH:16]=[C:15]([C:13]4[CH2:12][C:11](=[O:28])[NH:10][C:9]5[CH:29]=[C:30]([C:31]([F:33])([F:34])[F:32])[C:6]([N:5]([CH2:4][CH:1]6[CH2:2][CH2:3]6)[CH3:35])=[CH:7][C:8]=5[N:14]=4)[CH:20]=[CH:19][CH:18]=3)[N:22]=[N:23][CH:24]=2)[CH2:42][CH2:41]1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 186131737-(Cyclopropylmethyl-methyl-amino)-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 186131264-[3-(5-Cyclopropylaminomethyl-[1,2,3]triazol-1-yl)-phenyl]-7-(cyclopropylmethyl-methyl-amino)-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Procedure

The title compound was prepared from 7-(cyclopropylmethyl-methyl-amino)-4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 78) (145 mg, 0.3 mmol) by treatment with SOCl2 (3 eq.) and cyclopropyl amine (10 eq.) as described in Example 45. Obtained as a yellow solid (97 mg).

Sources & evidence

ORD record
ord-93723f76f1b04b46a8bdbdfa52a64620
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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