tert-Butanol → HCID 86615466, compound

HRID 1989653Notes

Reaction equation

HRID 1989653 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[C:8]([OH:12])([CH3:11])([CH3:10])[CH3:9].[CH3:13][C:14]1[N:19]=[C:18]([C:20]2[CH:21]=[C:22]([C:26]3[N:27]=[C:28]([NH2:31])[S:29][CH:30]=3)[CH:23]=[CH:24][CH:25]=2)[CH:17]=[C:16]([C:32]2[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=2)[CH:15]=1.C(N(CC)CC)C>ClCCl>[C:8]([O:12][C:6]([NH:5][S:2]([NH:31][C:28]1[S:29][CH:30]=[C:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:18]3[CH:17]=[C:16]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)[CH:15]=[C:14]([CH3:13])[N:19]=3)[CH:21]=2)[N:27]=1)(=[O:4])=[O:3])=[O:7])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 60209470HCID 60209470, compound

Product 1

HCID 86615466HCID 86615466, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled solution of commercially available chlorosulfonyl isocyanate (0.215 mL, 2.47 mmol) in dichloromethane (5 mL) was added tert-butanol (0.232 mL, 2.47 mmol) and the mixture was stirred at 0° C. for 30 min. Then 4-{3-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-phenyl}-thiazol-2-ylamine (example 342) (0.100 g, 0.243 mmol) and triethyl amine (0.42 mL, 2.96 mmol) were added and the mixture was stirred at 23° C. for 0.5 h. Diluted with DCM, washed with sat. NaHCO3-sol. and water, dried the organic layer over Na2SO4. Removal of the solvent in vacuum left a crude product which was purified by silica gel column chromatography with heptane/EtOAc/THF, followed by trituration with diethyl ether/heptane to give the title compound as a white solid (0.060 g, 42%). MS (ISP) 591.3 [(M+H)+]; mp 152° C. (dec.).

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. stirringthe mixture was stirred at 23° C. for 0.5 h
  3. washwashed with sat. NaHCO3-sol
  4. dry with materialand water, dried the organic layer over Na2SO4
  5. customRemoval of the solvent in vacuum
  6. waitleft a crude product which
  7. customwas purified by silica gel column chromatography with heptane/EtOAc/THF

Sources & evidence

ORD record
ord-b48772d1759c422a933cd43bce69d803
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

Loading…