tert-Butanol → HCID 56673857, compound

HRID 1524211Notes

Reaction equation

HRID 1524211 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].CC(O)(C)C.[CH:13]1[C:26]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][C:14]=1[C:27]1[N:31]([C:32]2[CH:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=2)[N:30]=[C:29]([C:39]([F:42])([F:41])[F:40])[CH:28]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:13]1[C:26]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][C:14]=1[C:27]1[N:31]([C:32]2[CH:33]=[CH:34][C:35]([NH:38][S:2]([NH2:5])(=[O:4])=[O:3])=[CH:36][CH:37]=2)[N:30]=[C:29]([C:39]([F:42])([F:40])[F:41])[CH:28]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 86700560HCID 86700560, compound

Product 1

HCID 56673857HCID 56673857, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Chlorosulfonyl isocyanate (1 mmol) was added dropwise to an ice-cold solution of t-BuOH (1 mmol) in CH2Cl2, which was then added to a mixture of 4-(5-phenanthren-2-yl-3-trifluoromethyl-pyrazol-1-yl)-phenylamine (1 mmol), generated from step d, and triethylamine (1.5 mmol) in CH2Cl2. The reaction mixture was stirred at 25° C. for 1 h, and concentrated. The residue was treated with 20% trifluoroacetic acid in CH2Cl2 for 3 h, washed with 10% NaHCO3, dried, and concentrated. The residue was purified by flash column chromatograph to give 36 as off-white solid in 78% yield. 1H NMR (DMSO-d6) δ 7.35-7.15 (m, 7H), 7.46 (dd, J=1.8, 8.7 Hz, 1H), 7.73-7.65 (m, 2H), 7.88 (dd, J=9, 33.6 Hz, 2H), 8.00-8.05 (m, 1H), 8.09 (d, J=1.8 Hz, 2H), 8.82 (m 2H), 9.89 (br s, 1H). HRMS exact mass of C24H17F3N4O2S, (M+Na)+. 505.0922 amu; found: 505.0902 amu. Anal. calcd C 59.75, H 3.55, N 11.61; found C 59,98, H 3.71, N 11.51.

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with 20% trifluoroacetic acid in CH2Cl2 for 3 h
  3. washwashed with 10% NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph

Sources & evidence

ORD record
ord-1a440e63741d49c0a2767f2132b6dee0
Source dataset
uspto-grants-2015_07
Patent number
US09079899B2

Reaction notes

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