Hydrochloric Acid → Hydrochloric Acid

HRID 28599Notes

Reaction equation

HRID 28599 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]1[O:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]3[CH:23]=[C:22]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=4[CH3:31])[N:21]=[C:20]([NH2:32])[N:19]=3)=[CH:13][CH:12]=2)[N:10]=1.CO.[OH-].[Na+].[ClH:38]>O>[NH2:32][C:20]1[N:19]=[C:18]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([C:9]3[N:10]=[C:6]([CH2:5][CH2:4][C:3]([OH:33])=[O:2])[O:7][CH:8]=3)=[CH:16][CH:15]=2)[CH:23]=[C:22]([C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=2[CH3:31])[N:21]=1.[ClH:38]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 68988417HCID 68988417, compound

Product 2

HCID 313Hydrochloric AcidHCID 426062843-(4-{4-[2-Amino-6-(5-chloro-2-methyl-phenyl)-pyrimidin-4-ylamino]-phenyl}-oxazol-2-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(4-{4-[2-amino-6-(5-chloro-2-methyl-phenyl)-pyrimidin-4-ylamino]-phenyl}-oxazol-2-yl)-propionic acid methyl ester (106 mg, 0.21 mmol), methanol (15 ml), and a solution of sodium hydroxide (500 mg, 12.5 mmol) in water (10 ml) was heated to 70° C. for 2 hours. After cooled to room temperature, the reaction mixture was neutralized to pH=1 using concentrated hydrochloric acid. Solid was collected via filtration and dried to give title compound in its hydrochloric acid salt form, (106 mg, 64% in two steps). 1H NMR (DMSO-d6) δ 2.40 (s, 3H, CH3), 2.76 (t, 2H, J=7.0 Hz, CH2), 3.04 (t, 2H, J=7.0 Hz, CH2), 6.57 (br s, 2H, NH2), 7.44 (d, 1H, J=8.2 Hz, Ar), 7.53-7.57 (m, 3H, Ar), 7.67 (d, 2H, J=8.7 Hz, Ar), 7.94-8.00 (m, 2H, Ar).

Workup

  1. filtrationSolid was collected via filtration
  2. customdried

Sources & evidence

ORD record
ord-439432c8efc4422f8744596ed0a01e0a
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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