1-Methylimidazole → HCID 86687532, compound

HRID 1473481Notes

Reaction equation

HRID 1473481 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23](Cl)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1.[S:27]1[CH:31]=[CH:30][N:29]=[C:28]1[NH2:32].CN1C=CN=C1>CC#N>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[C:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([NH:32][C:28]3[S:27][CH:31]=[CH:30][N:29]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 13901-MethylimidazoleHCID 21552-AminothiazoleHCID 86687533HCID 86687533, compound

Product 1

HCID 86687532HCID 86687532, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline-7-sulfonyl chloride (Intermediate DDDD; 2.040 g, 5.06 mmol) and thiazol-2-amine (2.54 g, 25.3 mmol) in 40 mL of MeCN was treated with 1-methylimidazole (0.496 ml, 5.06 mmol) and was heated to reflux with a heat gun, and then allowed to stir at room one hour. The reaction mixture was concentrated and the material was purified by silica gel column chromatography (0 to 100% EtOAc/heptane) to yield 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide (1.230 g, 2.64 mmol, 52.1% yield). 1H NMR (acetonitrile-d3) δ ppm: 9.42 (s, 1H), 8.52 (s, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.58 (d, J=7.4 Hz, 1H), 7.45-7.51 (m, 2H), 7.01 (d, J=4.8 Hz, 1H), 6.64 (d, J=4.7 Hz, 1H), 3.76 (s, 3H). m/z (ESI) 467.0 (M+H)+

Workup

  1. temperaturewas heated
  2. temperatureto reflux with a heat gun
  3. concentrationThe reaction mixture was concentrated
  4. customthe material was purified by silica gel column chromatography (0 to 100% EtOAc/heptane)

Sources & evidence

ORD record
ord-dd1e97990f184e688d063835913d4ff6
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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