Methanol → HCID 178524390, compound

HRID 606401Notes

Reaction equation

HRID 606401 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][C:22]3[N:26]=[CH:25][NH:24][N:23]=3)[CH:13]=2)=[O:9])=[N:5][C:4]2[S:27][CH:28]=[C:29]([CH2:30][O:31][CH2:32][C:33]3[CH:43]=[CH:42][C:36]([C:37]([O:39]CC)=[O:38])=[CH:35][CH:34]=3)[C:3]1=2.[OH-].[Na+].C1COCC1.CO>O>[O:1]=[C:2]1[NH:7][C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([O:18][CH2:19][CH2:20][CH2:21][C:22]3[N:26]=[CH:25][NH:24][N:23]=3)[CH:13]=2)=[O:9])=[N:5][C:4]2[S:27][CH:28]=[C:29]([CH2:30][O:31][CH2:32][C:33]3[CH:43]=[CH:42][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=3)[C:3]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178468934HCID 178468934, compound

Product 1

HCID 178524390HCID 178524390, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-[({[4-oxo-2-({[(2-{[3-(1H-1,2,4-triazol-3-yl)propyl]oxy}pyridin-4-yl)methyl]amino}carbonyl)-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl]methyl}oxy)methyl]benzoate obtained in Example 41 (309 mg, 0.512 mmol), 4N aqueous sodium hydroxide solution (0.64 mL, 2.6 mmol), THF (6 mL), methanol (6 mL) and water (6 mL) was stirred at 100° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid and methanol were added to the residue. The resulting crystals were recrystallized from ethyl acetate to give the title compound as a white powder (221 mg, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid and methanol
  2. additionwere added to the residue
  3. customThe resulting crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8befb677fa2f4f7bac632490629ffac5
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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