Sodium Carbonate → HCID 86681097, compound

HRID 1848124Notes

Reaction equation

HRID 1848124 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:33]=[CH:32][C:10]2[N:11]([CH2:14][C:15]3[CH:31]=[CH:30][C:18]4[N:19]=[C:20]([NH:22][C@@H:23]5[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]5[OH:29])[S:21][C:17]=4[CH:16]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)(C)C.C([O-])([O-])=O.[Na+].[Na+]>CO>[C:6]([C:7]1[CH:33]=[CH:32][C:10]2[N:11]([CH2:14][C:15]3[CH:31]=[CH:30][C:18]4[N:19]=[C:20]([NH:22][C@@H:23]5[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]5[OH:29])[S:21][C:17]=4[CH:16]=3)[CH:12]=[N:13][C:9]=2[CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86681096HCID 86681096, compound

Product 1

HCID 86681097HCID 86681097, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (1R,2R)-2-((6-((5-((trimethylsilyl)ethynyl)-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (61 mg, 0.13 mmole) and Na2CO3 (177 mg, 1.3 mmole) in MeOH (2 mL) was stirred at rt for 2 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by reverse-phase preparative HPLC using a mixture of water (5% CH3CN, 0.05% HCOOH) and CH3CN (0.05% HCOOH) as the mobile phase and a Varian Pursuit XRs C18 column as the stationary phase to afford (1R,2R)-2-((6-((5-ethynyl-1H-benzo[d]imidazol-1-yl)methyl)benzo[d]thiazol-2-yl)amino)cyclohexanol (8 mg, 17%) as a white powder. 1H NMR (300 MHz, DMSO-d6) δ 8.49 (s, 1H), 8.01 (d, J=7.3 Hz, 1H), 7.76 (s, 1H), 7.65 (s, 1H), 7.57 (d, J=8.3 Hz, 1H), 7.27-7.33 (m, 2H), 7.19 (m, 1H), 5.48 (s, 2H), 4.78 (d, J=4.9 Hz, 1H), 4.03 (s, 1H), 3.51 (m, 1H), 3.35 (m, 1H), 2.03 (m, 1H), 1.87 (m, 1H), 1.56-1.69 (m, 2H), 1.11-1.31 (m, 4H); LCMS (ESI) m/z 405 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by reverse-phase preparative HPLC
  4. additiona mixture of water (5% CH3CN, 0.05% HCOOH) and CH3CN (0.05% HCOOH) as the mobile phase

Sources & evidence

ORD record
ord-41c4a8d0de794c96ac0b4d51f0fa1692
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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