Pyrrolidine → HCID 15952079, compound

HRID 2244238Notes

Reaction equation

HRID 2244238 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([N:17]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[CH2:21][N:20]3[C:28]([C:31]([NH:33][CH2:34][C:35]4[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=4)=[O:32])=[CH:29][CH:30]=[C:19]3[CH2:18]2)=[O:16])=[CH:11][CH:10]=1)=O.[NH:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[N:37]1[CH:38]=[CH:39][CH:40]=[C:35]([CH2:34][NH:33][C:31]([C:28]2[N:20]3[C:19]([CH2:18][N:17]([C:15]([C:12]4[CH:11]=[CH:10][C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[CH2:1][N:41]5[CH2:45][CH2:44][CH2:43][CH2:42]5)=[CH:14][CH:13]=4)=[O:16])[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[CH2:21]3)=[CH:30][CH:29]=2)=[O:32])[CH:36]=1

Participants

6

Reactant 3

HCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 15952274HCID 15952274, compound

Product 1

HCID 15952079HCID 15952079, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 10-[(2′-formyl-1,1′-biphenyl-4-yl)carbonyl]-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 56, Step B (0.38 mmol), and pyrrolidine (0.80 mmol) in methanol (5 mL) was added a methanolic solution of sodium cyanoborohydride (0.2 M) and zinc chloride (0.1 M). The mixture was stirred at ambient temperature for 20 hours. The methanol was evaporated and the residue was taken up in chloroform and washed with 1.0 N sodium hydoxide, dried over anhydrous sodium sulfate, and evaporated. The solid was crystallized from ethyl acetate and hexane, m.p. 210-212° C.

Workup

  1. customThe methanol was evaporated
  2. washwashed with 1.0 N sodium hydoxide
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe solid was crystallized from ethyl acetate and hexane, m.p. 210-212° C.

Sources & evidence

ORD record
ord-97ca8372d10348fe989aa844196f3e28
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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