HCID 68208479, compound → HCID 67465250, compound

HRID 1429563Notes

Reaction equation

HRID 1429563 reaction equation
[CH3:1][C:2]([OH:41])([CH2:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:15][CH2:14][C:13]([C:16]2[CH:40]=[CH:39][C:19]3[N:20]=[C:21]([CH2:23][CH:24]4[CH2:29][CH2:28][N:27]([C:30]5[N:35]=[CH:34][C:33]([CH2:36][CH2:37][CH3:38])=[CH:32][N:31]=5)[CH2:26][CH2:25]4)[S:22][C:18]=3[CH:17]=2)=[CH:12][CH2:11]1)(=[O:9])=[O:8])[CH3:3]>CCOC(C)=O.[Pd]>[CH3:1][C:2]([OH:41])([CH2:4][CH2:5][CH2:6][S:7]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:40]=[CH:39][C:19]3[N:20]=[C:21]([CH2:23][CH:24]4[CH2:29][CH2:28][N:27]([C:30]5[N:31]=[CH:32][C:33]([CH2:36][CH2:37][CH3:38])=[CH:34][N:35]=5)[CH2:26][CH2:25]4)[S:22][C:18]=3[CH:17]=2)[CH2:12][CH2:11]1)(=[O:9])=[O:8])[CH3:3]

Participants

4

Reactant 1

HCID 68208479HCID 68208479, compound

Product 1

HCID 67465250HCID 67465250, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-5-(4-(2-((1-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)benzo[d]thiazol-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)pentan-2-ol (Example 41, 27 mg, 0.045 mmol) in EtOAc (1 mL) was added Pd/C (10%, 24 mg, 0.023 mmol). The mixture was stirred under a balloon of H2 for 24 h. The mixture was filtered through a pad of celite and the filtrate was concentrated to afford 2-methyl-5-(4-(2-((1-(5-propylpyrimidin-2-yl)piperidin-4-yl)methyl)benzo[d]thiazol-6-yl)piperidin-1-ylsulfonyl)pentan-2-ol (13 mg, 0.022 mmol, 48% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 2H), 7.92 (d, J=8.5 Hz, 1H), 7.68 (d, J=1.4 Hz, 1H), 7.30 (dd, J=8.4, 1.8 Hz, 1H), 4.71 (d, J=13.2 Hz, 2H), 4.01-3.94 (m, 2H), 3.05 (d, J=7.2 Hz, 2H), 3.03-2.97 (m, 2H), 2.95-2.89 (m, 2H), 2.89-2.83 (m, 2H), 2.80-2.70 (m, 1H), 2.38 (t, J=7.6 Hz, 2H), 2.24-2.13 (m, 1H), 2.03-1.93 (m, 4H), 1.92-1.81 (m, 4H), 1.66-1.59 (m, 2H), 1.59-1.51 (m, 2H), 1.36 (qd, J=12.4, 4.3 Hz, 2H), 1.27 (s, 6H), 1.26 (s, 1H), 0.93 (t, J=7.4 Hz, 3H). LCMS (m/z)=600 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1344a444b08f4ea2b592392f22799d1c
Source dataset
uspto-grants-2015_01
Patent number
US08940716B2

Reaction notes

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