2-Methylbenzoyl chloride → HCID 178492009, compound

HRID 1244374Notes

Reaction equation

HRID 1244374 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[NH:14][C:15]4[CH2:20][CH2:19][NH:18][CH2:17][C:16]=4[N:21]=3)[S:12][C:8]=2[C:7]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[C:37]1([CH3:46])[C:38]([C:43](Cl)=[O:44])=[CH:39][CH:40]=[CH:41][CH:42]=1>O1CCCC1>[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[NH:14][C:15]4[CH2:20][CH2:19][N:18]([C:43]([C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=5[CH3:46])=[O:44])[CH2:17][C:16]=4[N:21]=3)[S:12][C:8]=2[C:7]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 702762-Methylbenzoyl chlorideHCID 81531DiisopropylethylamineHCID 178492007HCID 178492007, compound

Product 1

HCID 178492009HCID 178492009, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.01 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine hydrochloride in 0.8 ml tetrahydrofurane were added at 0–4° C. 0.02 ml N-ethyldiisopropylamine and 0.004 ml o-toluoyl chloride. The mixture was refluxed over night, silicagel was added and the solvent was distilled off. The residue was transferred to a column prefilled with silicagel and was chromatographed with ethylacetate/methanol 98:2 to yield 0.006 g (50%)[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl]-o-tolyl-methanone as yellow solid; MS (ISP): m/e=490 (M+H+).

Workup

  1. additionwere added at 0–4° C
  2. temperatureThe mixture was refluxed over night
  3. additionsilicagel was added
  4. distillationthe solvent was distilled off
  5. customwas chromatographed with ethylacetate/methanol 98:2

Sources & evidence

ORD record
ord-5654247ef14b4e789e5c0436f547f168
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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