1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester → 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid

HRID 2250440Notes

Reaction equation

C([O:3][C:4]([C:6]1[N:19]([CH2:20][C:21]2[CH:25]=[C:24]([C:26]3[S:27][C:28]([Cl:31])=[CH:29][CH:30]=3)[O:23][N:22]=2)[C:9]2=[CH:10][N:11]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:13]=[C:8]2[CH:7]=1)=[O:5])C>C1COCC1.CO>[Cl:31][C:28]1[S:27][C:26]([C:24]2[O:23][N:22]=[C:21]([CH2:20][N:19]3[C:9]4=[CH:10][N:11]=[C:12]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:13]=[C:8]4[CH:7]=[C:6]3[C:4]([OH:5])=[O:3])[CH:25]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1.3 g (2.814 mmol) 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(2-methoxy-ethoxy)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester in 30 mL THF and 15 mL MeOH 11.26 mL 1M LiOH solution were added and the mixture was stirred at 50° C. for 3 h. The organic solvents were removed in vacuo, 50 mL of water were added and the pH was adjusted to pH 2 with 1N HCl solution. The desired product precipitated and was filtered, washed with water and dried over P2O5. Yield 1.11 g.

Workup

customThe organic solvents were removed in vacuo, 50 mL of water
additionwere added
customThe desired product precipitated
filtrationwas filtered
washwashed with water
dry with materialdried over P2O5

Sources & evidence

ORD record: ord-19f71d02c8dc44068a3879f400ebd557
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07317027B2

Reaction notes

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