Sodium borohydride → HCID 24785164, compound

HRID 1485356Notes

Reaction equation

HRID 1485356 reaction equation
[CH3:1][CH:2]([C:4]1[N:5]=[C:6]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([C:32](=[O:34])[CH3:33])=[CH:28][CH:27]=2)[C:7]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:10][CH2:9][C:8]=2[N:24]=1)[CH3:3].[BH4-].[Na+]>CO>[CH3:3][CH:2]([C:4]1[N:5]=[C:6]([NH:25][C:26]2[CH:27]=[CH:28][C:29]([CH:32]([OH:34])[CH3:33])=[CH:30][CH:31]=2)[C:7]2[CH2:13][CH2:12][N:11]([C:14]3[C:19]([C:20]([F:21])([F:23])[F:22])=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:10][CH2:9][C:8]=2[N:24]=1)[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58972605HCID 58972605, compound

Product 1

HCID 24785164HCID 24785164, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-({2-(1-methylethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl}amino)phenyl]ethanone (Example 96; 37 mg, 0.079 mmol) in MeOH was added NaBH4 (4.1 mg, 0.11 mmol). The mixture was stirred at rt for 4 h, then concentrated. The residue was redissolved in water and extracted with EtOAc. The organic layers were combined, dried, and concentrated. The crude residue was purified (FCC) to give the title compound (32.1 mg, 86%). MS (ESI): mass calcd. for C25H28F3N5O, 471.22; m/z found, 472.2 [M+H]+. 1H NMR (CDCl3): 8.40-8.38 (m, 1H), 7.87 (dd, J=7.8, 1.8 Hz, 1H), 7.67-7.64 (m, 2H), 7.38-7.34 (m, 2H), 6.97-6.92 (m, 1H), 6.51 (s, 1H), 4.93-4.88 (m, 1H), 3.69-3.60 (m, 4H), 3.24-3.18 (m, 2H), 3.06-2.98 (m, 1H), 2.98-2.94 (m, 2H), 1.76 (d, J=3.6 Hz, 1H), 1.52 (d, J=6.4 Hz, 3H), 1.31 (d, J=6.9 Hz, 6H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was redissolved in water
  3. extractionextracted with EtOAc
  4. customdried
  5. concentrationconcentrated
  6. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-ef0cbbaa92604d69aa67504ff3e68e27
Source dataset
uspto-grants-2016_08
Patent number
US09422293B2

Reaction notes

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