(1R,2R)-2-((6-((6-vinyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol → (1R,2R)-2-((6-((6-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol

HRID 1848088Notes

Reaction equation

HRID 1848088 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[N:11]=[CH:10][N:9]([CH2:12][C:13]3[CH:29]=[CH:28][C:16]4[N:17]=[C:18]([NH:20][C@@H:21]5[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]5[OH:27])[S:19][C:15]=4[CH:14]=3)[C:6]2=[N:7][CH:8]=1)=[CH2:2]>[Ni].CO.C1COCC1>[CH2:1]([C:3]1[CH:4]=[C:5]2[N:11]=[CH:10][N:9]([CH2:12][C:13]3[CH:29]=[CH:28][C:16]4[N:17]=[C:18]([NH:20][C@@H:21]5[CH2:26][CH2:25][CH2:24][CH2:23][C@H:22]5[OH:27])[S:19][C:15]=4[CH:14]=3)[C:6]2=[N:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 71548899(1R,2R)-2-((6-((6-vinyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol

Product 1

HCID 71549045(1R,2R)-2-((6-((6-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanolYield 30%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirred solution of (1R,2R)-2-((6-((6-vinyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (20 mg, 0.049 mmol) from Example 98 in 1:1 MeOH/THF (2 mL) was added Raney Ni (10 mg). The resulting mixture was stirred under a H2 balloon at rt for 4 h. LCMS analysis showed that the reaction was complete. The reaction mixture was filtered through a Celite plug and the filtrate was purified with preparative TLC to give (1R,2R)-2-((6-((6-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (6 mg, 30%). 1H NMR (300 MHz, DMSO-d6) δ 8.53 (br s, 1H), 8.26 (br s, 1H), 7.95 (d, J=12.4 Hz, 2H), 7.66 (br s, 1H), 7.25-7.42 (m, 1H), 7.06-7.25 (m, 1H), 5.45 (br s, 2H), 4.74 (d, J=4.5 Hz, 1H), 3.51 (br s, 1H), 2.73 (d, J=7.2 Hz, 2H), 2.04 (br s, 1H), 1.86 (br s, 1H), 1.62 (br s, 2H), 1.23 (t, J=6.8 Hz, 7H). LCMS (ESI) m/z 408 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite plug
  2. customthe filtrate was purified with preparative TLC

Sources & evidence

ORD record
ord-b13b4def14dc4745829fac990819dbb3
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

Loading…