Ethyl orthoformate → 6-((5-bromo-6-methoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole

HRID 1848007Notes

Reaction equation

HRID 1848007 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:23])[C:5]([NH:10][CH2:11][C:12]2[CH:22]=[CH:21][C:15]3[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=3[CH:13]=2)=[CH:6][C:7]=1[O:8][CH3:9].[CH2:24](OC(OCC)OCC)C>C(O)=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]2[N:10]([CH2:11][C:12]3[CH:22]=[CH:21][C:15]4[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=4[CH:13]=3)[CH:24]=[N:23][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 866810304-bromo-5-methoxy-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine

Product 1

HCID 866810316-((5-bromo-6-methoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazoleYield 40%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To a stirred mixture of 4-bromo-5-methoxy-N1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)benzene-1,2-diamine (120 mg, 0.3 mmol) from Step 2 of this Example and triethylorthoformate (20 mL) was added formic acid (1 mL). The mixture was heated under reflux for 2 h, then concentrated under reduced pressure. The residue was purified by silica gel flash chromatography eluting with 100% EtOAc to afford 6-((5-bromo-6-methoxy-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (50 mg, 40%) as an oil. 1H NMR (300 MHz, CDCl3) δ 8.01 (s, 1H), 7.78-7.91 (m, 2H), 7.46 (s, 1H), 7.25 (m, 1H), 6.69 (s, 1H), 5.42 (s, 2H), 3.81 (s, 3H), 2.78 (s, 3H). LCMS (ESI) m/z 420 and 422 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel flash chromatography
  5. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-5329249c8aa540a7b49a65772bceb158
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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