Chloroacetyl chloride → HCID 178422294, compound

HRID 2064618Notes

Reaction equation

HRID 2064618 reaction equation
[CH3:1][C:2]1[C:16]([CH3:17])=[CH:15][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH2:14])=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:28][C:29](Cl)=[O:30].[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>ClCCl>[CH3:17][C:16]1[C:2]([CH3:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3[C:13]([NH:14][C:29](=[O:30])[CH2:28][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)=[CH:12][NH:11][N:10]=3)=[N:6][C:5]=2[CH:15]=1

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 178422296HCID 178422296, compound

Product 1

HCID 178422294HCID 178422294, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine [100 mg, Example 233(c)] and diisopropylethylamine (307 μl) in dichloromethane (10 ml) was treated with chloroacetyl chloride (105 μl). The reaction mixture was stirred for 30 minutes at room temperature, then treated with morpholine (575 μl), then kept at room temperature overnight and then evaporated. The oily residue was partitioned between ethyl acetate and water and the organic phase was washed with water, then dried over magnesium sulfate and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate to give the N-[3-(5,6-dimethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-2-morpholin-4-yl-acetamide (49.9 mg) as an off-white solid. MS: 355.68 (M+H)+. HPLC (METHOD B1): RT=8.28 minutes.

Workup

  1. waitkept at room temperature overnight
  2. customevaporated
  3. customThe oily residue was partitioned between ethyl acetate and water
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-a657e61d70aa4211a99293fe14c38538
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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