Lithium Hydroxide → HCID 68208467, compound

HRID 1429553Notes

Reaction equation

HRID 1429553 reaction equation
C([O:4][CH2:5][C:6](=[O:44])[NH:7][CH2:8][CH2:9][S:10]([N:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:43]=[CH:42][C:22]3[N:23]=[C:24]([O:26][CH:27]4[CH2:32][CH2:31][N:30]([C:33]5[N:38]=[CH:37][C:36]([CH2:39][CH2:40][CH3:41])=[CH:35][N:34]=5)[CH2:29][CH2:28]4)[S:25][C:21]=3[CH:20]=2)=[CH:15][CH2:14]1)(=[O:12])=[O:11])(=O)C.[Li+].[OH-]>C1COCC1>[OH:4][CH2:5][C:6]([NH:7][CH2:8][CH2:9][S:10]([N:13]1[CH2:18][CH2:17][C:16]([C:19]2[CH:43]=[CH:42][C:22]3[N:23]=[C:24]([O:26][CH:27]4[CH2:28][CH2:29][N:30]([C:33]5[N:34]=[CH:35][C:36]([CH2:39][CH2:40][CH3:41])=[CH:37][N:38]=5)[CH2:31][CH2:32]4)[S:25][C:21]=3[CH:20]=2)=[CH:15][CH2:14]1)(=[O:11])=[O:12])=[O:44]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54596662HCID 54596662, compound

Product 1

HCID 68208467HCID 68208467, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-oxo-2-(2-(4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)ethylamino)ethyl acetate (32 mg, 0.05 mmol) in THF (1 mL) was added LiOH (saturated, aqueous, 0.5 mL). The mixture was stirred at rt overnight. It was extracted with DCM (3×2 mL). The combined organic layers were dried (Na2SO4), filtered, concentrated to afford the desired product as a white solid (28 mg, 95% purity, 89% yield). 1H NMR (400 MHz, CDCl3) δ 8.16 (s, 2H), 7.63 (m, 2H), 7.38 (m, 1H), 6.06 (m, 1H), 5.43 (m, 1H), 3.75 (m, 12H), 2.88-0.72 (m, 17H). LCMS (m/z)=601 (M+H)+.

Workup

  1. extractionIt was extracted with DCM (3×2 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb660fcf9d648c9a82055c69ad5077c
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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