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

HRID 1098823Notes

Reaction equation

HRID 1098823 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-433d5ac471e040f0b7a9c35eab361a06
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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