Acetyl chloride → HCID 178492008, compound

HRID 1244375Notes

Reaction equation

HRID 1244375 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](Cl)(=[O:39])[CH3:38]>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:37](=[O:39])[CH3:38])[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 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 178492007HCID 178492007, compound

Product 1

HCID 178492008HCID 178492008, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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 0.002 ml acetyl chloride in 0.25 ml tetrahydrofurane. 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 95:5 to yield 0.009 g (89%) 1-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl]-ethanone as yellow solid; M.p.: 155–157° C.; MS (ISP): m/e=414 (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 95:5

Sources & evidence

ORD record
ord-da8d62101015498eb5c8b3f5ff52667a
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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