Dichloromethane → HCID 136409074, 화합물

HRID 1473692노트

반응식

HRID 1473692 반응식
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

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 86687532HCID 86687532, 화합물

생성물 1

HCID 136409074HCID 136409074, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-39c3cd5637284f6ea58b5ab65a5a9c7d
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

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