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1-(Benzenesulfonyl)-1H-indol-5-amine → Acetic Acid 3-[4-(1-benzenesulfonyl-1H-indol-5-ylamino)-quinazolin-6-yl]-allyl ester

HRID 1264057
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인쇄 미리보기

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HRID 1264057 반응식
O([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:16]=2)[N:11]=[CH:10][N:9]=1)C1C=CC=CC=1.[NH2:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH:30]=[CH:29]2>C1(O)C=CC=CC=1>[C:38]1([S:35]([N:31]2[C:32]3[C:28](=[CH:27][C:26]([NH:25][C:8]4[C:17]5[C:12](=[CH:13][CH:14]=[C:15]([CH:18]=[CH:19][CH2:20][O:21][C:22](=[O:24])[CH3:23])[CH:16]=5)[N:11]=[CH:10][N:9]=4)=[CH:34][CH:33]=3)[CH:29]=[CH:30]2)(=[O:36])=[O:37])[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 154501451-(Benzenesulfonyl)-1H-indol-5-amineHCID 69484701Acetic Acid 3-(4-phenoxy-quinazolin-6-yl)-allyl ester

생성물 1

HCID 54063371Acetic Acid 3-[4-(1-benzenesulfonyl-1H-indol-5-ylamino)-quinazolin-6-yl]-allyl ester수율 43%

시약·촉매·용매 1

HCID 996Phenol용매

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온도
100 °C

실험 절차

A mixture of ester 26 (630 mg, 1.97 mmol) and 5-amino-1-phenylsulfonylindole in phenol (3.0 g) was heated at 100° C. for 20 hours. Excess phenol was removed by distillation and the resulting brown oil was purified by silica gel chromatography eluting with 1:1 ethyl acetate:hexanes then ethyl acetate. Quinazoline 27 (430 mg, 43%) was obtained as an off-white waxy solid. 1H NMR (CDCl3; 400 MHz): δ: 8.61 (s, 1H), 7.92 (m, 3H), 7.82 (m, 4H), 7.51 (m, 2H), 7.43 (m, 3H), 6.74 (d, 1H), 6.62 (d, 1H), 6.45 (dt, 1H), 4.74 (dd, 2H), 2.09 (s, 3H).

후처리

  1. customExcess phenol was removed by distillation
  2. customthe resulting brown oil was purified by silica gel chromatography
  3. washeluting with 1:1 ethyl acetate

출처 및 근거

ORD 기록
ord-4a236376a3d4400e86e075b7f4696192
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06541481B2

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