Trifluoroacetic acid → HCID 136337770, 화합물

HRID 1917731노트

반응식

HRID 1917731 반응식
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]([NH:26][C:27]([NH:29][C:30]4[CH:34]=[C:33]([C:35]([CH3:38])([CH3:37])[CH3:36])[O:32][N:31]=4)=[O:28])[CH:23]=[CH:24][CH:25]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[C:35]([C:33]1[O:32][N:31]=[C:30]([NH:29][C:27]([NH:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:13]3[C:12]4[C:17](=[CH:18][C:9]([OH:8])=[CH:10][CH:11]=4)[N:16]=[CH:15][N:14]=3)[CH:21]=2)=[O:28])[CH:34]=1)([CH3:38])([CH3:36])[CH3:37]

참가 물질

3

반응물 2

HCID 6422Trifluoroacetic acidHCID 668764501-(3-(7-(Benzyloxy)quinazolin-4-yloxy)phenyl)-3-(5-tert-butylisoxazol-3-yl)urea

생성물 1

HCID 136337770HCID 136337770, 화합물수율 60.1%

반응 조건

온도
85 °C

실험 절차

1-(3-(7-(Benzyloxy)quinazolin-4-yloxy)phenyl)-3-(5-tert-butylisoxazol-3-yl)urea (725 mg, 1.42 mmol) was treated with trifluoroacetic acid (7 mL) and heated at 85° C. for 3 h. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate/water. The solution was neutralized with saturated sodium bicarbonate (pH=8) and the organic layer separated. After extraction of the aqueous phase with ethyl acetate, the organic fractions were combined, dried (MgSO4) and concentrated under reduced pressure. The solid was triturated with ethyl acetate to afford 1-(5-tert-butylisoxazol-3-yl)-3-(3-(7-hydroxyquinazolin-4-yloxy)phenyl)urea (358 mg, 60%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.92 (s, 1H), 9.64 (s, 1H), 9.07 (s, 1H), 8.58 (s, 1H), 8.24 (d, 1H), 7.57 (s, 1H), 7.41 (t, 1H), 7.30 (d, 2H), 7.20 (s, 1H), 6.97 (d, 1H) 6.49 (s, 1H), 1.27 (s, 9H); LC-MS (ESI) m/z 420 (M+H)+.

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate/water
  3. customthe organic layer separated
  4. extractionAfter extraction of the aqueous phase with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe solid was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-2e7cc3fe22e047c993495bf5a89a69bb
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618289B2

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