Dimethylamine → 7-Dimethylamino-4-[3-(3-dimethylaminomethyl-isoxazol-5-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265798Notes

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]([C:18]4[O:22][N:21]=[C:20]([CH2:23]O)[CH:19]=4)[CH:13]=3)=[N:11][C:5]=2[CH:4]=1.O=S(Cl)Cl.[NH:37]([CH3:39])[CH3:38]>>[CH3:1][N:2]([CH3:32])[C:3]1[C:27]([C:28]([F:31])([F:29])[F:30])=[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]([C:18]4[O:22][N:21]=[C:20]([CH2:23][N:37]([CH3:39])[CH3:38])[CH:19]=4)[CH:13]=3)=[N:11][C:5]=2[CH:4]=1

Participants

Reactant 3

HCID 674Dimethylamine

HCID 24386Thionyl Chloride

HCID 186133087-Dimethylamino-4-[3-(3-hydroxymethyl-isoxazol-5-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 186131097-Dimethylamino-4-[3-(3-dimethylaminomethyl-isoxazol-5-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-(3-hydroxymethyl-isoxazol-5-yl)-phenyl]-8-trifluoromethyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 46) (53 mg, 0.12 mmol) by treatment with SOCl2 (3 eq.) and 40% aqueous Me2NH-sol. (10 eq.) as described in Example 45. Obtained as a light yellow solid (21 mg).

Sources & evidence

ORD record: ord-a2c0b72ffc104c42a6e3654c31e1faf2
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544985B2

Reaction notes

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