Hydrochloric Acid → HCID 131729417, compound

HRID 424136Notes

Reaction equation

HRID 424136 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].[ClH:40]>O1CCOCC1>[ClH:40].[ClH:40].[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24829325HCID 24829325, compound

Product 1

HCID 131729417HCID 131729417, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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, 220 mg, 0.41 mmol) in 1,4-dioxane (10 mL) was dropwise added hydrochloric acid (30 mg, 0.82 mmol). The precipitate that formed was filtered and washed with dioxane, followed by hexanes. The solid was then recrystallized from dioxane/methanol to give the desired product salt as a white powder (240 mg, 95%). MS m/z 533.3 (M+H)+; calcd. mass 532. Retention time (LC-MS): 3.13 min. 1H-NMR (DMSO-d6): δ 9.10 (s, broad, 1H); 8.97 (s, 1H); 8.87 (m, 1H); 8.53 (d, J=5.6 Hz, 1H); 8.21 (t, 1H); 7.50 (m, 3H); 7.39 (m, 2H); 7.33 (m, 1H); 7.20 (m, 1H); 7.06 (m, 1H); 6.39 (s, 1H); 4.58 (s, 2H); 2.79 (d, J=4.8 Hz, 3H); 1.27 (s, 9H).

Workup

  1. customThe precipitate that formed
  2. filtrationwas filtered
  3. washwashed with dioxane
  4. customThe solid was then recrystallized from dioxane/methanol

Sources & evidence

ORD record
ord-b33f00d0dd5845019ce4512235c3c2ba
Source dataset
uspto-grants-2012_01
Patent number
US08101773B2

Reaction notes

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