HCID 10029454, compound → HCID 10323129, compound

HRID 854756Notes

Reaction equation

HRID 854756 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:34])[CH:12]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)[CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[N:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:34])[CH:12]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[C:22]([C:30]([F:32])([F:33])[F:31])[CH:21]=2)[CH2:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 10029454HCID 10029454, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10323129HCID 10323129, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 6-[2-(4-methylsulfonyl-3-trifluoromethyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionylamino]-nicotinic acid methyl ester (prepared as in Example 15, 129 mg, 0.25 mmol) in ethyl ether (6 mL) cooled to 0° C. was treated with a 1.0M solution of lithium aluminum hydride solution in diethyl ether (0.30 mL, 0.30 mmol). The orange-colored reaction mixture was stirred at 0° C. for 1 h. The reaction was then quenched by the dropwise addition of water (10 mL) and extracted with ethyl acetate (2×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S Silica, 8/2 hexanes/ethyl acetate) afforded N-(5-hydroxymethyl-pyridin-2-yl)-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-3-(tetrahydro-pyran-2-yl)-propionamide (44 mg, 36%) as a cream foam: EI-HRMS m/e calcd for C22H25F3N2O5S (M+H)+ 487.1509. found 487.1514.

Workup

  1. customThe reaction was then quenched by the dropwise addition of water (10 mL)
  2. extractionextracted with ethyl acetate (2×10 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a51d2b9a14ed49c5b8751dc44e5e64a5
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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