Cyclopentanecarboxylic acid → N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-(3-methoxyphenyl)propan-2-yl]cyclopentanecarboxamide

HRID 13058

Reaction equation

HRID 13058 reaction equation
[CH:1]1([C:6]([OH:8])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][C@H:26]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)[C@@H:27]([NH2:29])[CH3:28])=[CH:22][CH:23]=3)[CH:18]=[N:17]2)=[CH:12][CH:11]=1>ClCCl>[F:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[C:24]3[C:19](=[CH:20][C:21]([O:25][C@H:26]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)[C@@H:27]([NH:29][C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)=[O:8])[CH3:28])=[CH:22][CH:23]=3)[CH:18]=[N:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 18840Cyclopentanecarboxylic acidHCID 59339733(1R,2S)-1-(1-(4-fluorophenyl)indazol-5-yloxy)-1-(3-methoxyphenyl)propan-2-amine

Product 1

HCID 25012194N-[(1R,2S)-1-[1-(4-fluorophenyl)indazol-5-yl]oxy-1-(3-methoxyphenyl)propan-2-yl]cyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,1-carbonyldiimidazole (12 mg, 70 μmol) in dichloromethane (1 ml) was added cyclopentanecarboxylic acid (11 μl, 100 μmol) to give a colorless solution. The reaction mixture was stirred for 1 h at r.t. Then a solution of (1R,2S)-1-{[1-(4-fluorophenyl)-1H-indazol-5-yl]oxy}-1-(3-methoxyphenyl)propan-2-amine (6a, 19 mg, 50 μmol) in dichloromethane (0.5 ml) was added, and the stirring was continued at r.t. overnight. The solvent was removed in vacuo, the residue dissolved in acetonitrile/water mixture, and the crude product purified by preparative HPLC. Yield 18 mg (76%).

Workup

  1. customto give a colorless solution
  2. waitthe stirring was continued at r.t. overnight
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in acetonitrile/water mixture
  5. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-105ac68a9d904dd4bcd2b0ac87f84a82
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Linked notes

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