Potassium Carbonate → HCID 71548897, compound

HRID 1848079Notes

Reaction equation

HRID 1848079 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]2[N:15]=[CH:14][N:13]([CH2:16][C:17]3[CH:33]=[CH:32][C:20]4[N:21]=[C:22]([NH:24][C@@H:25]5[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]5[OH:31])[S:23][C:19]=4[CH:18]=3)[C:10]2=[N:11][CH:12]=1)(C)C.C([O-])([O-])=O.[K+].[K+]>CO>[C:6]([C:7]1[CH:8]=[C:9]2[N:15]=[CH:14][N:13]([CH2:16][C:17]3[CH:33]=[CH:32][C:20]4[N:21]=[C:22]([NH:24][C@@H:25]5[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]5[OH:31])[S:23][C:19]=4[CH:18]=3)[C:10]2=[N:11][CH:12]=1)#[CH:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86681060HCID 86681060, compound

Product 1

HCID 71548897HCID 71548897, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (1R,2R)-2-((6-((6-((trimethylsilyl)ethynyl)-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (100 mg, 0.21 mmol) from Step 3 of this Example in MeOH (5 mL) was added excess K2CO3 (150 mg). The resulting mixture was stirred at rt for 30 min. LCMS analysis showed that the reaction was complete. The reaction mixture was filtered through a Celite plug and the filtrate was purified by preparative HPLC using a mixture of water (5% CH3CN, 0.05% AcOH) and CH3CN (0.05% AcOH) as the mobile phase and Varian Pursuit XRs Diphenyl column as the stationary phase to afford (1R,2R)-2-((6-((6-ethynyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol as a tan powder (40 mg, 47%). 1H NMR (300 MHz, DMSO-d6) δ 8.69 (s, 1H), 8.50 (d, J=1.5 Hz, 1H), 8.23 (d, J=1.7 Hz, 1H), 8.02 (d, J=6.6 Hz, 1H), 7.66 (s, 1H), 7.26-7.34 (m, 1H), 7.15-7.26 (m, 1H), 5.49 (s, 2H), 4.29 (s, 1H), 3.26-3.38 (m, 2H), 2.03 (d, J=10.4 Hz, 1H), 1.85 (br s, 1H), 1.62 (d, J=4.7 Hz, 2H), 1.00-1.38 (m, 4H). LCMS (ESI) m/z 404 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through a Celite plug
  2. customthe filtrate was purified by preparative HPLC
  3. additiona mixture of water (5% CH3CN, 0.05% AcOH) and CH3CN (0.05% AcOH) as the mobile phase and Varian Pursuit XRs Diphenyl column as the stationary phase

Sources & evidence

ORD record
ord-54fcfc51c23940499fa3e63d4765998c
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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