Methanol → HCID 178524496, compound

HRID 606406Notes

Reaction equation

[O:1]=[C:2]1[NH:7][C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][CH2:20][O:21][C:22]3[N:26]=[CH:25][NH:24][N:23]=3)[CH:13]=2)=[O:9])=[N:5][C:4]2[CH:27]=[N:28][N:29]([CH2:30][CH2:31][O:32][C:33]3[CH:42]=[CH:41][C:36]([C:37]([O:39]C)=[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][CH:15]=[C:14]([O:18][CH2:19][CH2:20][O:21][C:22]3[N:26]=[CH:25][NH:24][N:23]=3)[CH:13]=2)=[O:9])=[N:5][C:4]2[CH:27]=[N:28][N:29]([CH2:30][CH2:31][O:32][C:33]3[CH:34]=[CH:35][C:36]([C:37]([OH:39])=[O:38])=[CH:41][CH:42]=3)[C:3]1=2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of methyl 4-({2-[7-oxo-5-({[(3-{[2-(1H-1,2,4-triazol-3-yloxy)ethyl]oxy}phenyl)methyl]amino}carbonyl)-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-1-yl]ethyl}oxy)benzoate obtained in Example 47 (164 mg, 0.285 mmol), 4N aqueous sodium hydroxide solution (0.250 mL), THF (2 mL), methanol (2 mL) and water (2 mL) was stirred at 90° C. for 2 hr. The solvent was evaporated under reduced pressure, and the residue was diluted with water (20 mL), and acidified with 1N hydrochloric acid (1.5 mL). The precipitated solid was collected by filtration, and washed with water (4 mL×2) and methanol (4 mL). The obtained solid was recrystallized from methanol to give the title compound as a white powder (120 mg, 75%).

Workup

customThe solvent was evaporated under reduced pressure
additionthe residue was diluted with water (20 mL)
filtrationThe precipitated solid was collected by filtration
washwashed with water (4 mL×2) and methanol (4 mL)
customThe obtained solid was recrystallized from methanol

Sources & evidence

ORD record: ord-871893bfaf1a44d6acb991b87b11926d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915267B2

Reaction notes

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