Sodium Hydroxide → HCID 24810288, compound

HRID 2081105Notes

Reaction equation

[OH-].[Na+].C([O:5][C:6]([C:8]1[C:9]2[S:17][CH:16]=[C:15]([CH2:18][O:19][C:20]3[CH:25]=[C:24]([C:26]4[O:27][C:28]([C:31]5[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=5)=[N:29][N:30]=4)[CH:23]=[CH:22][C:21]=3[CH3:38])[C:10]=2[C:11]([NH2:14])=[N:12][CH:13]=1)=[O:7])C>O1CCCC1.CO>[NH2:14][C:11]1[C:10]2[C:15]([CH2:18][O:19][C:20]3[CH:25]=[C:24]([C:26]4[O:27][C:28]([C:31]5[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=5)=[N:29][N:30]=4)[CH:23]=[CH:22][C:21]=3[CH3:38])=[CH:16][S:17][C:9]=2[C:8]([C:6]([OH:7])=[O:5])=[CH:13][N:12]=1

Participants

Conditions

Temperature: 50 °C

Procedure

An aqueous solution of sodium hydroxide (2 N, 2.0 mL, 1.0 mmol) was added to a solution of 4-amino-3-{5-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (0.22 g, 0.42 mmol) (from Example 47 supra) in tetrahydrofuran/methanol (3:1, 8 mL) and the mixture was heated at 50° C. for 1 day. The reaction mixture was concentrated and azeotroped with toluene. The solid residue was triturated with ethyl acetate. The solid was then suspended in water and treated with hydrochloric acid (1 N). After stirring 30 minutes, the solid was collected, washed with water and dried to give 4-amino-3-{5-[5-(4-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-methyl-phenoxymethyl}-thieno[3,2-c]pyridine-7-carboxylic acid. (Yield 0.20 g, 95%).

Workup

concentrationThe reaction mixture was concentrated
customazeotroped with toluene
customThe solid residue was triturated with ethyl acetate
additiontreated with hydrochloric acid (1 N)
customthe solid was collected
washwashed with water
customdried

Sources & evidence

ORD record: ord-5eb635e0b4344aeda39e06dae142b8c3
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932390B2

Reaction notes

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