Methanol → HCID 59300486, compound

HRID 603458Notes

Reaction equation

HRID 603458 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH2:34][CH2:35][CH3:36])[CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C@H:24]([CH2:28][C:29]([O:31]CC)=[O:30])[CH2:23][CH2:22]4)=[N:12][CH:13]=2)[S:5][C:6]=1[CH3:7].CO.O.[Li+].[OH-]>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([N:14]([CH2:34][CH2:35][CH3:36])[CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C@H:24]([CH2:28][C:29]([OH:31])=[O:30])[CH2:23][CH2:22]4)=[N:12][CH:13]=2)[S:5][C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 59300495HCID 59300495, compound

Product 1

HCID 59300486HCID 59300486, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ((1S)-5-{3-[[5-(4,5-dimethyl-1,3-thiazol-2-yl)-2-pyridinyl](propyl)amino]-propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 267) (70 mg, 0.15 mmol) in a mixture of THF (2 mL), methanol (2 mL), and water (1 mL) was added LiOH (40 mg, 1.74 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 using H3PO4 (5% solution in water). The aqueous phase was extracted with ethyl acetate, and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to provide the product (56 mg, 86%). 1H NMR (400 MHz, DMSO-d6) δ 8.44 (d, 1H), 7.80 (d, 1H), 7.06 (d, 1H), 6.79 (d, 1H), 6.71 (dd, 1H), 6.56 (d, 1H), 3.95 (t, 2H), 3.62 (t, 2H), 3.44-3.25 (m, 3H), 2.81-2.62 (m, 3H), 2.30-2.23 (m, 8H), 1.99-1.96 (m, 2H), 1.65-1.53 (m, 3H), 0.87 (t, 3H); LC-MS: RT=2.73 min, (M+H)+ 480.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e573271b868a49f39a9908cd1e828977
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

Loading…