{1-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzylcarbamoyl]-8-fluoro-1,2-dihydroquinolin-4-yl}acetic acid ethyl ester → {1-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzylcarbamoyl]-8-fluoro-1,2,3,4-tetrahydroquinolin-4-yl}acetic acid ethyl ester

HRID 558954Notes

Reaction equation

HRID 558954 reaction equation
[CH2:1]([O:3][C:4](=[O:44])[CH:5]=[C:6]1[C:15]2[C:10](=[C:11]([F:16])[CH:12]=[CH:13][CH:14]=2)[N:9]([C:17](=[O:43])[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]3[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH2:32][N:31]4[CH:39]=[CH:40][CH:41]=[C:30]4[CH2:29]3)=[O:27])=[CH:22][C:21]=2[CH3:42])[CH2:8][CH2:7]1)[CH3:2].C(OC(=O)CC1C2C(=C(F)C=CC=2)N(C(=O)NCC2C=CC(C(N3C4C=CC=CC=4CN4C=CC=C4C3)=O)=CC=2C)CC=1)C>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:44])[CH2:5][CH:6]1[C:15]2[C:10](=[C:11]([F:16])[CH:12]=[CH:13][CH:14]=2)[N:9]([C:17](=[O:43])[NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([N:28]3[C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH2:32][N:31]4[CH:39]=[CH:40][CH:41]=[C:30]4[CH2:29]3)=[O:27])=[CH:22][C:21]=2[CH3:42])[CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 59807184{1-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzylcarbamoyl]-8-fluoro-1,2-dihydroquinolin-4-yl}acetic acid ethyl esterHCID 67000028{1-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzylcarbamoyl]-8-fluoro-2,3-dihydro-1H-quinolin-4-ylidene}acetic acid ethyl ester

Product 1

HCID 11563353{1-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzylcarbamoyl]-8-fluoro-1,2,3,4-tetrahydroquinolin-4-yl}acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture (75 mg, 0.13 mmol) of {1-[4-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methylbenzylcarbamoyl]-8-fluoro-2,3-dihydro-1H-quinolin-4-ylidene}acetic acid ethyl ester from Example 4 and {1-[4-(5H,11H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methyl-benzylcarbamoyl]-8-fluoro-1,2-dihydroquinolin-4-yl]acetic acid ethyl ester from Example 5 was dissolved in methanol (50 ml). To the solution was added a catalytic amount of 10% palladium on carbon and the mixture was stirred under a hydrogen atmosphere for 6 h. The mixture was filtered through Celite® and evaporated. The mixture was redissolved in methanol (50 ml), a further catalytic amount of 10% palladium on carbon was added and the mixture stirred under a hydrogen atmosphere for 3 h. The mixture was filtered and evaporated to give a white solid, yield 74 mg (97%).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. customevaporated
  3. dissolutionThe mixture was redissolved in methanol (50 ml)
  4. additiona further catalytic amount of 10% palladium on carbon was added
  5. stirringthe mixture stirred under a hydrogen atmosphere for 3 h
  6. filtrationThe mixture was filtered
  7. customevaporated
  8. customto give a white solid, yield 74 mg (97%)

Sources & evidence

ORD record
ord-6bf069291a764f6dbcb427be93d17069
Source dataset
uspto-grants-2011_11
Patent number
US08063038B2

Reaction notes

Loading…