Triethylamine → HCID 42635071, compound

HRID 1009006Notes

Reaction equation

HRID 1009006 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:12]3[S:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:11]=3[CH:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.C1(O[C:34](Cl)=[O:35])C=CC=CC=1.[Br:37][C:38]1[S:42][C:41]([NH2:43])=[N:40][CH:39]=1>C(#N)C>[Br:37][C:38]1[S:42][C:41]([NH:43][C:34]([NH:19][S:16]([C:14]2[S:13][C:12]3[C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[CH:8][CH:9]=[CH:10][C:11]=3[CH:15]=2)(=[O:18])=[O:17])=[O:35])=[N:40][CH:39]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 436002-Thiazolamine, 5-bromo-HCID 67305542HCID 67305542, compound

Product 1

HCID 42635071HCID 42635071, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 7-pyridin-4-yl-benzo[b]thiophene-2-sulfonic acid amide (0.10 g, 0.34 mmol) in acetonitrile (3 mL) were added triethylamine (0.11 mL, 0.8 mmol) and at 0-5° C. phenylchloroformate (0.065 g, 0.40 mmol). The mixture was stirred at rt for 2 h, and 5-bromo-thiazol-2-yl-amine (0.092 g, 0.50 mmol) was added. The reaction mixture was stirred at 55-60° C. for 3 h. After cooling down to rt, the solution was chromatographed over silica gel using dichloromethane/methanol as eluent to obtain the title compound (0.045 g) as a light brown solid. MS (ISN) m/e 492.8, 494.8 (M−H)−

Workup

  1. customat 0-5° C.
  2. stirringThe reaction mixture was stirred at 55-60° C. for 3 h
  3. temperatureAfter cooling down to rt
  4. customthe solution was chromatographed over silica gel

Sources & evidence

ORD record
ord-36192bb43abc47b1b9c565c15dbe989f
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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