Dichloromethane → HCID 136409074, compound

HRID 1473692Notes

Reaction equation

HRID 1473692 reaction equation
C[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:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1.C(Cl)Cl.B(Br)(Br)Br>C(OCC)(=O)C>[OH: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:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)(=[O:24])=[O:25])=[CH:20][CH:21]=2)[N:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86687532HCID 86687532, compound

Product 1

HCID 136409074HCID 136409074, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A vial was charged with 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide (Example 261; 0.100 g, 0.214 mmol) and DCM (2.144 ml) to give a clear solution. Boron tribromide (0.101 ml, 1.072 mmol) was added in one portion at room temperature to give a dark red suspension. The mixture was stirred overnight. The reaction was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-10% MeOH:DCM) to afford 4-(2-hydroxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinazoline-7-sulfonamide as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=13.02 (s, 1H), 10.65 (s, 1H), 9.49 (s, 1H), 8.41 (d, J=1.5 Hz, 1H), 8.02-7.96 (m, 1H), 7.94-7.88 (m, 1H), 7.63 (d, J=7.7 Hz, 1H), 7.38 (d, J=8.1 Hz, 1H), 7.34 (s, 1H), 7.31 (d, J=4.6 Hz, 1H), 6.90 (d, J=4.5 Hz, 1H). m/z (ESI) 453.2 (M+H)+.

Workup

  1. customto give a clear solution
  2. customto give a dark red suspension
  3. washwashed with saturated sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe material was purified via column chromatography (RediSep Gold 40 g, gradient elution 0-10% MeOH:DCM)

Sources & evidence

ORD record
ord-39c3cd5637284f6ea58b5ab65a5a9c7d
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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