Water → HCID 57471430, compound

HRID 1044530Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl[1-(3,5-difluorobenzyl)-7-(2-{[(1-methyl-1H-pyrrol-3-yl)sulfonyl]amino}ethoxy)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (200 mg, 0.365 mmol) was dissolved in tetrahydrofuran (16 mL). A 1 M solution of lithium aluminium hydride in tetrahydrofuran (0.73 mL, 0.73 mmol) was added dropwise at room temperature. The reaction mixture was heated to 50° C. for 2 h. Under cooling 2N sodium hydroxide solution (3 mL) was added dropwise. Water (30 mL) and ethyl acetate (30 mL) were added. The aqueous phase was extracted twice with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 61 mg (0.116 mmol, 32%).

Workup

additionwas added dropwise
extractionThe aqueous phase was extracted twice with ethyl acetate
dry with materialThe combined extracts were dried (MgSO4)
customthe solvent was evaporated in vacuo
customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record: ord-f9e53a1b6b9b4427b231682711cff3eb
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563617B2

Reaction notes

Loading…