Cyclopropanecarbonyl chloride → HCID 11539924, compound

HRID 2102368Notes

Reaction equation

HRID 2102368 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=4)[NH2:25])=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH:38]1([C:41](Cl)=[O:42])[CH2:40][CH2:39]1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[C:24]([NH:25][C:41]([CH:38]5[CH2:40][CH2:39]5)=[O:42])[CH:26]=[CH:27][CH:28]=4)=[N:14][CH:13]=[N:12][C:11]=3[S:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 11646895HCID 11646895, compound

Product 1

HCID 11539924HCID 11539924, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)aniline (10 mg, 0.025 mmol), diisopropylethylamine (13 mg, 0.10 mmol), and dichloromethane (2 mL) was treated with cyclopropanecarbonyl chloride (30 mg, 0.028 mmol) and stirred at room temperature for 6 hours. The solvent was removed in vacuo and the remaining residue was dissolved in ethyl acetate (25 mL), washed with aqueous sodium bicarbonate solution (2×20 mL), and the organic fraction was separated and concentrated. The product was purified by column chromatography over silica gel using 1% methanol and 0.01% ammonia in 1:1 ethyl acetate/hexanes to give 12 mg (quantitative yield) of N-[3-(3-{[5-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy}propoxy)phenyl]cyclopropanecarboxamide as a yellow gum. MS [M+H] 464.0,

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe remaining residue was dissolved in ethyl acetate (25 mL)
  3. washwashed with aqueous sodium bicarbonate solution (2×20 mL)
  4. customthe organic fraction was separated
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography over silica gel using 1% methanol and 0.01% ammonia in 1:1 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b35e5bf44bde4416b10e72ad6f0cbb5f
Source dataset
uspto-grants-2009_08
Patent number
US07576080B2

Reaction notes

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