tert-Butanol → HCID 68695466, compound

HRID 1928364Notes

Reaction equation

HRID 1928364 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:25]=[CH:24][N:23]=[C:22]([C:26]3[CH:27]=[C:28]([NH2:32])[CH:29]=[CH:30][CH:31]=3)[N:21]=2)[CH:17]=[C:16]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[CH:15]=1.C(N(CC)CC)C>ClCCl>[C:8]([O:12][C:6]([NH:5][S:2]([NH:32][C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([C:22]2[N:21]=[C:20]([C:18]3[CH:17]=[C:16]([C:33]4[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=4)[CH:15]=[C:14]([CH3:13])[N:19]=3)[CH:25]=[CH:24][N:23]=2)[CH:27]=1)(=[O:4])=[O:3])=[O:7])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 24760586HCID 24760586, compound

Product 1

HCID 68695466HCID 68695466, compoundYield 35%

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 3-{4-[6-methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-pyrimidin-2-yl}-phenylamine (example 326) (0.200 g, 0.494 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 to give the title compound as an off-white solid (0.100 g, 35%). MS (ISP) 586.2 [(M+H)+].

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-0fbf27a8423a4b45832f6f06ee9971e1
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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