Chloride → 7-(Isobutyl-methyl-amino)-8-methyl-4-[3-(5-pyrrolidin-1-ylmethyl-[1,2,4]triazol-1-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265887Notes

Reaction equation

HRID 1265887 reaction equation
OC[C:3]1[N:7]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([CH3:32])[C:24]([N:26]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:27])=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[N:6]=[N:5][CH:4]=1.S(Cl)(Cl)=O.[Cl-].N1[CH2:42][CH2:41][CH2:40][CH2:39]1.[CH3:43][N:44](C=O)C>ClCCl>[CH2:28]([N:26]([CH3:27])[C:24]1[C:23]([CH3:32])=[CH:22][C:17]2[NH:18][C:19](=[O:21])[CH2:20][C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([N:7]4[C:3]([CH2:4][N:5]5[CH2:39][CH2:40][CH2:41][CH2:42]5)=[N:44][CH:43]=[N:6]4)[CH:9]=3)=[N:15][C:16]=2[CH:25]=1)[CH:29]([CH3:31])[CH3:30]

Participants

7

Reactant 5

HCID 312ChlorideHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 186131914-[3-(5-Hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Product 1

HCID 186133567-(Isobutyl-methyl-amino)-8-methyl-4-[3-(5-pyrrolidin-1-ylmethyl-[1,2,4]triazol-1-yl)-phenyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 4-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]-7-(isobutyl-methyl-amino)-8-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 132) (180 mg, 0.42 mmol) by reaction with thionylchloride in dichloromethane and subsequent treatment of the corresponding chloride with pyrrolidine in DMF according to the method described in Example 45. Obtained as an off-white solid (106 mg, 52%).

Sources & evidence

ORD record
ord-8e98b3492e7e4a8496ceeb06f453bd0b
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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