Chloride → HCID 18613522, compound

HRID 1265868Notes

Reaction equation

HRID 1265868 reaction equation
O[CH2:2][C:3]1[N:7]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:15][C:16](=[O:33])[NH:17][C:18]4[CH:24]=[C:23]([C:25]#[N:26])[C:22]([N:27]([CH2:29][CH:30]([CH3:32])[CH3:31])[CH3:28])=[CH:21][C:19]=4[N:20]=3)[CH:11]=[CH:12][CH:13]=2)[N:6]=[N:5][CH:4]=1.S(Cl)(Cl)=O.[Cl-].[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>ClCCl.CN(C=O)C>[CH2:29]([N:27]([CH3:28])[C:22]1[C:23]([C:25]#[N:26])=[CH:24][C:18]2[NH:17][C:16](=[O:33])[CH2:15][C:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([N:7]4[C:3]([CH2:2][N:39]5[CH2:43][CH2:42][CH2:41][CH2:40]5)=[CH:4][N:5]=[N:6]4)[CH:9]=3)=[N:20][C:19]=2[CH:21]=1)[CH:30]([CH3:31])[CH3:32]

Participants

7

Reactant 4

HCID 312ChlorideHCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 18613128HCID 18613128, compound

Product 1

HCID 18613522HCID 18613522, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 2-[3-(5-hydroxymethyl-[1,2,3]triazol-1-yl)-phenyl]8-(isobutyl-methyl-amino)-4-oxo-4,5-dihydro-3H -benzo[b][1,4]diazepine-7-carbonitrile (Example 111) (200 mg, 0.45 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 a light yellow solid (140 mg, 63%).

Sources & evidence

ORD record
ord-df64828ca3464863872f407a229ccb89
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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