Hydrochloric Acid → HCID 58316983, compound

HRID 1187313Notes

Reaction equation

HRID 1187313 reaction equation
C[O:2][C:3](=[O:37])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[C:19]([C:20](=[O:36])[C:21]4[C:26]([F:27])=[CH:25][CH:24]=[C:23]([NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])[C:22]=4[F:35])=[CH:18][NH:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:6][CH:5]=1.CO.[OH-].[Na+].Cl>O1CCCC1>[F:35][C:22]1[C:23]([NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])=[CH:24][CH:25]=[C:26]([F:27])[C:21]=1[C:20]([C:19]1[C:12]2[C:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:37])=[O:2])=[CH:9][CH:8]=3)=[N:16][CH:15]=[N:14][C:13]=2[NH:17][CH:18]=1)=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58316799HCID 58316799, compound

Product 1

HCID 58316983HCID 58316983, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{5-[2,6-Difluoro-3-(propane-1-sulfonylamino)-benzoyl]-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino}-benzoic acid methyl ester (P-1162, 26 mg, 0.05 mmol) is combined with 1 mL of methanol is added, 0.5 mL of tetrahydrofuran, and 0.5 mL of 2 M sodium hydroxide. The reaction is stirred at room temperature for 48 hours, then neutralized with 1 M hydrochloric acid and the volatile solvents are removed under vacuum. The remaining aqueous suspension is filtered to collect the solids, which are dried under vacuum to provide the desired compound (P-1163, 25 mg). MS (ESI) [M+H+]+=516.0.

Workup

  1. additionis added
  2. customthe volatile solvents are removed under vacuum
  3. filtrationThe remaining aqueous suspension is filtered
  4. customto collect the solids, which
  5. customare dried under vacuum

Sources & evidence

ORD record
ord-3bdc947a5cf24da08d915c73dc080674
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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