Acetyl chloride → HCID 24991775, compound

HRID 2251080Notes

Reaction equation

HRID 2251080 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:33])[C:9]1[N:24]([C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[F:32])[C:12]2[N:13]=[C:14]([NH:17][CH:18]([CH3:23])[C:19]([CH3:22])([OH:21])[CH3:20])[N:15]=[CH:16][C:11]=2[CH:10]=1.C(N(CC)CC)C.[C:41](Cl)(=[O:43])[CH3:42].C(OCC)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:33][C:41](=[O:43])[CH3:42])[C:9]1[N:24]([C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[F:32])[C:12]2[N:13]=[C:14]([NH:17][CH:18]([CH3:23])[C:19]([OH:21])([CH3:22])[CH3:20])[N:15]=[CH:16][C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 69217202HCID 69217202, compound

Product 1

HCID 24991775HCID 24991775, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-[6-[(2-chloro-phenyl)-hydroxy-methyl}-7-(2,6-difluoro-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-2-methyl-butan-2-ol, 9, (0.47 g, 1.00 mmol) and triethylamine (0.60 ml, 4.0 mmol), in pyridine (5 ml) is added dropwise acetyl chloride (0.08 ml, 2.20 mmol). The reaction mixture is stirred under argon at room temperature for 48 hours. Ethyl acetate is added to the mixture and the resulting mixture is washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting residue is purified over silica (40% EtOAc/hexanes) to afford 30 mg of the desired: 1H NMR (300 MHz, CDCl3) δ 8.42 (s, 1H), 7.52-7.10 (m, 7H), 6.11 (d, J=5.3 Hz, 1H), 4.00-3.91 (m, 1H), 1.97 (d, J=5.9 Hz, 3H), 1.50 (br s, 1H), 1.23 (s, 3H), 1,19 (s, 3H); HRMS calcd for C26H25ClF2N4O3 (M+H)+ 515.1662, found 515.1644.

Workup

  1. washthe resulting mixture is washed with water, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue is purified over silica (40% EtOAc/hexanes)
  6. customto afford 30 mg of the

Sources & evidence

ORD record
ord-28f8fd1a87494247b6a4ec5328010885
Source dataset
uspto-grants-2008_01
Patent number
US07319102B1

Reaction notes

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