Butyryl chloride → 1-{3-[4-(5H,11H-Pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-pyrazol-1-yl}-butan-1-one

HRID 1635828Notes

Reaction equation

HRID 1635828 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][C:9]([C:12]([N:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[CH2:18][N:17]4[CH:25]=[CH:26][CH:27]=[C:16]4[CH2:15]3)=[O:13])=[CH:8][CH:7]=2)=[N:2]1.[C:28](Cl)(=[O:32])[CH2:29][CH2:30][CH3:31]>N1C=CC=CC=1>[CH:27]1[CH:26]=[CH:25][N:17]2[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[N:14]([C:12]([C:9]3[CH:10]=[CH:11][C:6]([C:3]4[CH:4]=[CH:5][N:1]([C:28](=[O:32])[CH2:29][CH2:30][CH3:31])[N:2]=4)=[CH:7][CH:8]=3)=[O:13])[CH2:15][C:16]=12

Participants

4

Reactant 2

HCID 8855Butyryl chlorideHCID 178519422HCID 178519422, compound

Product 1

HCID 103100881-{3-[4-(5H,11H-Pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-phenyl]-pyrazol-1-yl}-butan-1-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In the manner of Example 32, employing [4-(1H-pyrazol-3-yl)-phenyl]-(5H,11H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-methanone (0.71 g) in dry pyridine (10 ml) and butyryl chloride (0.32 g), the title compound (0.54 g) was obtained as a solid, m.p. 105-110° C.; MS, m/z: 424 (M)+.

Sources & evidence

ORD record
ord-f36d27303fd9465bb20cceab05c5e313
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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