Sulfuric Acid → HCID 131729418, compound

HRID 424137Notes

Reaction equation

HRID 424137 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:30]=[CH:29][C:17]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:27][CH3:28])=[O:26])[CH:20]=3)=[CH:16][C:15]=2[F:31])=[O:12])[N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][OH:39])[CH:33]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[S:40](=[O:44])(=[O:43])([OH:42])[OH:41]>CC(C)=O.C(OCC)(=O)C>[S:40]([OH:44])([OH:43])(=[O:42])=[O:41].[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:30]=[CH:29][C:17]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25]([NH:27][CH3:28])=[O:26])[CH:20]=3)=[CH:16][C:15]=2[F:31])=[O:12])[N:7]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][OH:39])[CH:33]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 24829325HCID 24829325, compound

Product 1

HCID 131729418HCID 131729418, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-{4-[({3-tert-butyl-1-[3-(hydroxymethyl)phenyl]-1H-pyrazol-5-yl}carbamoyl)amino]-3-fluorophenoxy}-N-methylpyridine-2-carboxamide, 400 mg, 0.751 mmol) in acetone (5 mL) was dropwise added a solution of sulfuric acid (500 mg, 5.1 mmol) in ethyl acetate (5 mL) The precipitate that formed was filtered and washed with acetone, followed by hexane to give the desired product salt as a crystalline white powder (460 mg, 97%). MS m/z 533.4 (M+H)+; calcd. mass 532. Retention time (LC-MS): 3.20 min. 1H-NMR (DMSO-d6): δ 9.02 (m, 1H); 8.88 (m, 2H); 8.52 (d, J=6.0 Hz, 1H); 8.22 (m, 1H); 7.50 (m, 2H); 7.42 (m, 1H); 7.37 (m, 2H); 7.32 (m, 1H); 7.19 (m, 1H); 7.05 (m, 1H); 6.39 (s, 1H); 4.57 (s, 2H); 2.78 (m, 3H); 1.26 (s, 9H).

Workup

  1. customthat formed
  2. filtrationwas filtered
  3. washwashed with acetone

Sources & evidence

ORD record
ord-a064ad274b564901a129781d306f3aa3
Source dataset
uspto-grants-2012_01
Patent number
US08101773B2

Reaction notes

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