Methanol → HCID 59300465, compound

HRID 603467Notes

Reaction equation

HRID 603467 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C@H:25]([CH2:29][C:30]([O:32]CC)=[O:31])[CH2:24][CH2:23]4)[CH:12]=[CH:11][C:10]=2[C:35]([F:38])([F:37])[F:36])=[CH:5][CH:4]=1.CO.O.[Li+].[OH-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[C:13]([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C@H:25]([CH2:29][C:30]([OH:32])=[O:31])[CH2:24][CH2:23]4)[CH:12]=[CH:11][C:10]=2[C:35]([F:37])([F:38])[F:36])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59300550HCID 59300550, compound

Product 1

HCID 59300465HCID 59300465, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [(1S)-5-(3-{[6-(4-methoxyphenyl)-5-(trifluoromethyl)-2-pyridinyl]amino}propoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 304, 0.05 g, 0.09 mmol) in a mixture of THF (1 mL), methanol (1 mL), and water (0.5 mL) was added LiOH (0.02 g, 0.85 mmol). The mixture was stirred at rt for 18 h, and then concentrated under reduced pressure. The residue was taken up in water and acidified with 5% H3PO4. The aqueous solution was extracted with ethyl acetate. The combined organic phases dried (Na2SO4), filtered, and concentrated under reduced pressure to give the product (0.038 g, 88%). 1H NMR (400 MHz, CD2Cl2) δ 7.65 (d, 1H), 7.35 (d, 2H), 7.05 (d, 1H), 6.92 (d, 2H), 6.73 (s, 1H), 6.66 (dd, 1H), 6.49 (d, 1H), 4.02 (t, 2H), 3.84 (s, 3H), 3.55 (t, 3H), 3.45 (qt, 1H), 2.92-2.65 (m, 3H), 2.40-2.30 (m, 2H), 2.10-2.02 (m, 2H), 1.80-1.68 (m, 1H); LC-MS: RT=3.02 min, (M+H)+ 531.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe aqueous solution was extracted with ethyl acetate
  3. dry with materialThe combined organic phases dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3232b1732da44cd2ac513abd80de8d98
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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