Water → 10-(9H-Fluoren-2-ylcarbonyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244299Notes

Reaction equation

HRID 2244299 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:33]=[CH:32][C:31]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:24][C:23]=4[CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[NH2:36][CH2:37][C:38]1[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=1.O>O1CCOCC1>[CH:22]1[C:23]2[CH2:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]=2[CH:32]=[CH:33][C:21]=1[C:19]([N:10]1[C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][N:14]2[C:5]([C:3]([NH:36][CH2:37][C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)=[O:4])=[CH:6][CH:7]=[C:8]2[CH2:9]1)=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 310183-PyridinemethanamineHCID 686864232,2,2-Trichloro-1-[10-(9H-fluorene-2-carbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanone

Product 1

HCID 1595297910-(9H-Fluoren-2-ylcarbonyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.7 g (0.0014 mol) of 2,2,2-trichloro-1-[10-(9H-fluorene-2-carbonyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]-ethanone of Step B and 0.30 g (0.0028 mol) of 3-aminomethylpyridine in 25 mL of 1,4-dioxane was heated under reflux for 1 hour. The reaction mixture was cooled to room temperature and poured into 75 mL of water with stirring. The precipitate was collected, washed with water, and recrystallized from ethanol to provide the title compound, m.p. 116-119° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. customThe precipitate was collected
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-647e9fdf23ab42c8bdc42145b2548a37
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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