Triethylamine → HCID 42635069, compound

HRID 1009004Notes

Reaction equation

HRID 1009004 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[S:10]([NH2:13])(=[O:12])=[O:11].C(N(CC)CC)C.C1(O[C:28](Cl)=[O:29])C=CC=CC=1.[NH2:31][C:32]1[S:33][C:34]([Br:37])=[CH:35][N:36]=1>C(#N)C>[Br:37][C:34]1[S:33][C:32]([NH:31][C:28]([NH:13][S:10]([C:2]2[NH:1][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)(=[O:11])=[O:12])=[O:29])=[N:36][CH:35]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 436002-Thiazolamine, 5-bromo-HCID 142563011H-Indole-2-sulfonamide

Product 1

HCID 42635069HCID 42635069, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 1H-indole-2-sulfonic acid amide (Graham, S., Hoffman, J. Med. Chem., 33(2), 749-754 (1990); 0.235 g, 1.2 mmol) in acetonitrile (15 mL) was added at 10° C. triethylamine (0.4 mL), followed dropwise over 5 minutes by a solution of chloroformic acid phenyl ester (0.22 g, 1.4 mmol) in acetonitrile (2 mL). The reaction mixture was stirred at rt for 1 h and 2-amino-5-bromothiazole (0.225 g, 1.3 mmol) was added. The reaction mixture was stirred at 55° C. for 2 h. The precipitate that was formed was filtered off, washed with acetonitrile and ether and dried to obtain the title compound (0.18 g) as a pink solid. MS (ISN) m/e 399.0, 400.9 (M−H)−

Workup

  1. stirringThe reaction mixture was stirred at 55° C. for 2 h
  2. customThe precipitate that was formed
  3. filtrationwas filtered off
  4. washwashed with acetonitrile and ether
  5. customdried

Sources & evidence

ORD record
ord-b5ced83dc57e40f3931d3cbfc039a8c9
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

Loading…