Diisopropylethylamine → HCID 11282527, compound

HRID 1244367Notes

Reaction equation

HRID 1244367 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[NH:22][C:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:15]=4[N:14]=3)[S:12][C:8]=2[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:6][CH:5]=1.C(N(C(C)C)C(C)C)C.[CH3:38][O:39][CH2:40][C:41](Cl)=[O:42]>O1CCCC1>[CH3:38][O:39][CH2:40][C:41]([N:19]1[CH2:20][CH2:21][C:15]2[N:14]=[C:13]([C:11]3[S:12][C:8]4[C:7]([N:23]5[CH2:24][CH2:25][O:26][CH2:27][CH2:28]5)=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[C:9]=4[N:10]=3)[NH:22][C:16]=2[CH2:17][CH2:18]1)=[O:42]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 96623Methoxyacetyl chlorideHCID 114415902-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine hydrochloride

Product 1

HCID 11282527HCID 11282527, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.13 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine hydrochloride in 10 ml tetrahydrofurane were added at 0–4° C. 0.21 ml N-ethyldiisopropylamine and 0.037 g methoxyacetyl chloride. The mixture was refluxed for 17 hours, silicagel was added and the solvent was distilled off. The residue was transferred to a column prefilled with silicagel and was chromatographed with dichloromethane/methanol 96:4 to yield 0.126 g (91%) 2-methoxy-1-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl]-ethanone as yellow solid; MS (ISP): m/e=458 (M+H+).

Workup

  1. additionwere added at 0–4° C
  2. temperatureThe mixture was refluxed for 17 hours
  3. additionsilicagel was added
  4. distillationthe solvent was distilled off
  5. customwas chromatographed with dichloromethane/methanol 96:4

Sources & evidence

ORD record
ord-a508f01eef57437a86ef30ff5dae69ac
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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