Water → HCID 57471430, compound

HRID 510548Notes

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-b58b0b47afae490bbe9b3c3a8aff9f6b
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096619B2

Reaction notes

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