Ethyl orthoformate → HCID 86681012, compound

HRID 1847978Notes

Reaction equation

HRID 1847978 reaction equation
[CH2:1](OC(OCC)OCC)C.[CH3:11][O:12][C:13]1[N:18]=[C:17]([NH:19][CH2:20][C:21]2[CH:31]=[CH:30][C:24]3[N:25]=[C:26]([S:28][CH3:29])[S:27][C:23]=3[CH:22]=2)[C:16]([NH2:32])=[CH:15][CH:14]=1>>[CH3:11][O:12][C:13]1[N:18]=[C:17]2[N:19]([CH2:20][C:21]3[CH:31]=[CH:30][C:24]4[N:25]=[C:26]([S:28][CH3:29])[S:27][C:23]=4[CH:22]=3)[CH:1]=[N:32][C:16]2=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 86681011HCID 86681011, compound

Product 1

HCID 86681012HCID 86681012, compoundYield 53%

Procedure

To a solution of triethoxymethane (5 mL) was added 6-methoxy-N2-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyridine-2,3-diamine (332 mg, 1.0 mmol) from Step 6 of this Example at rt. The reaction mixture was heated under reflux overnight. After cooling to rt, the mixture was concentrated under reduced pressure. The crude product was purified on a silica gel column using a mixture of EtOAc-CH2Cl2 (0 to 100%, v/v) as eluent to give 6-((5-methoxy-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-2-(methylthio)benzo[d]thiazole as a brown solid (180 mg, 53%). 1H NMR (300 MHz, CDCl3) δ 7.95 (d, J=8.7 Hz, 1H), 7.87 (s, 1H), 7.82 (d, J=8.5 Hz, 1H), 7.70 (d, J=1.1 Hz, 1H), 7.41 (dd, J=1.7, 8.3 Hz, 1H), 6.71 (d, J=8.7 Hz, 1H), 5.47 (s, 2H), 3.99 (s, 3H), 2.78 (s, 3H). LCMS (ESI) m/z 343 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe crude product was purified on a silica gel column
  5. additiona mixture of EtOAc-CH2Cl2 (0 to 100%, v/v) as eluent

Sources & evidence

ORD record
ord-4f2011188e88494e871c48c6f11e78d9
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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