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Triethylamine → N-(3-Hydroxy-4-methyl-phenyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzamide

HRID 883867
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HRID 883867 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH3:9])=[CH:4][CH:3]=1.[CH:10]([C:13]1[CH:14]=[CH:15][C:16]2[C:21]([NH:22][C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=3[S:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:26](Cl)=[O:27])=[N:20][CH:19]=[N:18][C:17]=2[N:41]=1)([CH3:12])[CH3:11].C(N(CC)CC)C>ClCCl>[OH:8][C:6]1[CH:7]=[C:2]([NH:1][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:31]([S:32][C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)=[C:23]([NH:22][C:21]3[C:16]4[CH:15]=[CH:14][C:13]([CH:10]([CH3:11])[CH3:12])=[N:41][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:24]=2)[CH:3]=[CH:4][C:5]=1[CH3:9]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 178185-Amino-2-methylphenolHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride

생성물 1

HCID 67040159N-(3-Hydroxy-4-methyl-phenyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzamide수율 65%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

A solution of 5-amino-o-cresol (20.4 mg, 0.1655 mmol) and the product from Example 14B (70 mg, 0.1655 mmol) in dichloromethane (4 mL) was treated with triethylamine (0.025 mL, 0.1806 mmol) at room temperature. The resulting solution was stirred for 18 hours. The reaction mixture was then washed with water and brine, and the combined organic layers were dried over MgSO4, the concentrated under vacuum to give a residue which was purified by silica gel chromatography using methanol and dichloromethane as eluent to provide the title compound (55 mg, 65%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6H), 2.07 (s, 3H), 3.17-3.28 (m, 1H), 3.77 (s, 3H), 6.86-7.10 (m, 5H), 7.30-7.46 (m, 3H), 7.64 (d, J=7.35 Hz, 1H), 7.72-7.86 (m, 1H), 7.95 (s, 1H), 8.43-8.68 (m, 1H), 8.77-8.97 (m, 1H), 9.27-9.46 (m, 1H), 10.02 (s, 1H), 10.21-10.40 (m, 1H); MS (APCI) m/z 552 (M+H)+.

후처리

  1. washThe reaction mixture was then washed with water and brine
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. concentrationthe concentrated under vacuum
  4. customto give a residue which
  5. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2f961c33e1ca4a37be0da1ae42fb8433
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236950B2

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