Ethanamine, 2,2,2-trifluoro- → 7-Dimethylamino-4-(3-{5-[(2,2,2-trifluoro-ethylamino)methyl]-[1,2,3]triazol-1-yl}-phenyl)8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265819Notes

Reaction equation

HRID 1265819 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.[F:37][C:38]([F:42])([F:41])[CH2:39][NH2:40]>>[CH3:32][N:2]([CH3:1])[C:3]1[C:27]([C:28]([F:30])([F:31])[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][NH:40][CH2:39][C:38]([F:42])([F:41])[F:37])=[CH:21][N:20]=[N:19]4)[CH:13]=3)=[N:11][C:5]=2[CH:4]=1

Participants

4

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 24386Thionyl ChlorideHCID 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 186135137-Dimethylamino-4-(3-{5-[(2,2,2-trifluoro-ethylamino)methyl]-[1,2,3]triazol-1-yl}-phenyl)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) (133 mg, 0.3 mmol) by treatment with SOCl2 (3 eq.) and 2,2,2-trifluoroethylamine (10 eq.) as described in Example 45. Obtained as a light yellow solid (19 mg).

Sources & evidence

ORD record
ord-50c86fac41434ccba0d85a94623fef36
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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