Acetyl chloride → HCID 68814580, compound

HRID 2105235Notes

Reaction equation

HRID 2105235 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][NH:6][C:7]([C:9]1[N:14]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:21]=2)[N:12]=[C:11]([NH:31][C:32]2[CH:36]=[C:35]([CH3:37])[NH:34][N:33]=2)[CH:10]=1)=[O:8].C(N(CC)CC)C.C1C[O:48][CH2:47][CH2:46]1>>[C:1]([NH:5][NH:6][C:7]([C:9]1[N:14]=[C:13]([N:15]2[CH2:19][CH2:18][CH2:17][CH:16]2[C:20]2[O:24][N:23]=[C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[CH:21]=2)[N:12]=[C:11]([NH:31][CH:32]2[CH:36]=[C:35]([CH3:37])[NH:34][N:33]2[C:47](=[O:48])[CH3:46])[CH:10]=1)=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11293765HCID 11293765, compound

Product 1

HCID 68814580HCID 68814580, compoundYield 96%

Procedure

Acetyl chloride (0.28 ml, 3.94 mmol) was added to a mixture of 6-hydrazide-2-{2-[3-(pyrid-2-yl)isoxazol-5-yl]pyrrolidin-1-yl}-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidine (Example 77) (800 mg, 1.79 mmol) and triethylamine (0.6 ml, 4.13 mmol) in anhydrous THF (20 ml) at 0° C. The reaction was allowed to warm to ambient temperature and stirred for a further 1 hour. The volatiles were removed by evaporation and the residue triturated with water and collected by filtration to give the title compound (911 mg, 96%).

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue triturated with water
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c779c68afe52459a9add968bd0061561
Source dataset
uspto-grants-2009_08
Patent number
US07579349B2

Reaction notes

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