Sodium borohydride → HCID 69087658, compound

HRID 1047088Notes

Reaction equation

HRID 1047088 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)=[CH:6][CH:5]=1)([O-])=O.[BH4-].[Na+]>C1COCC1.CO.Cl[Ni]Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3([NH:38][C:39](=[O:45])[O:40][C:41]([CH3:43])([CH3:42])[CH3:44])[CH2:35][CH2:36][CH2:37]3)=[CH:30][CH:29]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 68067477HCID 68067477, compound

Product 1

HCID 69087658HCID 69087658, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (1-{4-[2-(4-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (317 mg, 0.49 mmol) in THF (10 mL) and MeOH (5 mL) cooled to 0° C. was added NiCl2 (245 mg, 1.03 mmol) and NaBH4 (84 mg, 2.04 mmol). The reaction was slowly allowed to warm to room temperature and stirred 30 min. The reaction was diluted with sat.NaHCO3aq and extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine. The organic phase was dried over sodium sulfate, filtered and concentrated gave the title compound as a yellow solid (214 mg, 76%).

Workup

  1. additionThe reaction was diluted with sat.NaHCO3aq and
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washwashed with brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e6aa9696096f4f2eb82fc2af31e5b677
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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