Ammonium Chloride → HCID 69217202, compound

HRID 2251079Notes

Reaction equation

HRID 2251079 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[N:25]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[C:13]2[N:14]=[C:15]([NH:18][C@@H:19]([CH3:24])[C:20]([OH:23])([CH3:22])[CH3:21])[N:16]=[CH:17][C:12]=2[CH:11]=1)=[O:9].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:9])[C:10]1[N:25]([C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])[C:13]2[N:14]=[C:15]([NH:18][CH:19]([CH3:24])[C:20]([CH3:22])([OH:23])[CH3:21])[N:16]=[CH:17][C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 24990692HCID 24990692, compound

Product 1

HCID 69217202HCID 69217202, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-(2-chloro-phenyl)-[7-(2,6-difluoro-phenyl)-2-(2-hydroxy-1,2-dimethyl-propylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-methanone, 8, (1.0 g, 2.1 mmol) in ethanol (2.4 mL) is added sodium borohydride (0.3 g, 8.5 mmol) and the mixture stirred overnight at room temperature. Aqueous ammonium chloride solution is then added and the mixture is extracted with EtOAc several times and the organic phases combined washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting residue is purified over silica (50% EtOAc/hexanes, then 100% EtOAc) to afford 470 mg of the desired product as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 1H), 7.44-7.36 (m, 2H), 7.22-7.17 (m, 3H), 7.08 (t, J=8.8 Hz, 2H), 6.95 (dd, J=8.4, 8.0 Hz, 1H), 6.32 (d, J=13.2 Hz, 1H), 6.00 (s, 1H), 3.81 (m, 1H), 1.12-1.08 (m, 9H); HRMS calcd for C24H23ClF2N4O2 (M+H)+ 473.1556, found 473.1542.

Workup

  1. extractionthe mixture is extracted with EtOAc several times
  2. washthe organic phases combined washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified over silica (50% EtOAc/hexanes

Sources & evidence

ORD record
ord-2c86c3eadc7540e0b0b291f6609e6cb0
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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