Trifluoroacetic acid → 3-[5-Amino-4-benzoyl-3-(piperidin-4-yloxy)-pyrazol-1-yl]-n-cyclopropyl-4-methyl-benzamide, trifluoroacetate salt

HRID 2041045Notes

Reaction equation

HRID 2041045 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:19]([C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:18]([NH2:28])[N:17]([C:29]3[CH:34]=[C:33]([C:35](=[O:40])[NH:36][CH:37]4[CH2:39][CH2:38]4)[CH:32]=[CH:31][C:30]=3[CH3:41])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[NH2:28][C:18]1[N:17]([C:29]2[CH:34]=[C:33]([CH:32]=[CH:31][C:30]=2[CH3:41])[C:35]([NH:36][CH:37]2[CH2:38][CH2:39]2)=[O:40])[N:16]=[C:15]([O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:19]=1[C:20](=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 111572374-[5-amino-4-benzoyl-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-pyrazol-3-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 112731323-[5-Amino-4-benzoyl-3-(piperidin-4-yloxy)-pyrazol-1-yl]-n-cyclopropyl-4-methyl-benzamide, trifluoroacetate saltYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-amino-4-benzoyl-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-pyrazol-3-yloxy]-piperidine-1-carboxylic acid tert-butyl ester 8 (5.0 mg, 0.0089 mmol) in dichloromethane (2.0 ml) was added trifluoroacetic acid (0.5 ml). The mixture was stirred at room temperature for 3 h. Volatiles were removed in vacuo and the residue was washed with ether and a small amount of EtOAc to give the desired 3-[5-amino-4-benzoyl-3-(piperidin-4-yloxy)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamide, trifluoroacetate salt 9 as a white solid (3.0 mg, 59%). HPLC (4 minute 10-90 gradient) tR 1.75 min; MS m/z 460.1 [M+H]+; 1H NMR (DMSO-d6, 300 MHz) δ 8.50 (d, J=4.0, 1H), 8.33 (bs, 2H), 7.90 (d, J=8.0, 1H), 7.83 (s, 1H), 7.62 (d, J=7.0, 2 H), 7.44-7.52 (m, 4H), 7.03 (bs, 2H), 4.82 (m, 1H), 2.97 (m, 2H), 2.85 (m, 1H), 2.73 (m, 2H), 2.27 (s, 3H), 1.91 (m, 2H), 1.73 (m, 2H), 0.71 (m, 2H), 0.57 (m, 2H) ppm.

Workup

  1. customVolatiles were removed in vacuo
  2. washthe residue was washed with ether

Sources & evidence

ORD record
ord-804eca54449d47b18ea755748c2dd999
Source dataset
uspto-grants-2013_11
Patent number
US08580838B2

Reaction notes

Loading…