1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3,4-dichlorophenyl)-7-{(2E)-4-[isopropyl(methyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

HRID 1887427노트

반응식

HRID 1887427 반응식
Br[CH2:2][CH:3]=[CH:4][C:5]([OH:7])=O.[CH:8]([NH:11][CH3:12])([CH3:10])[CH3:9].[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:34]3[C:33]4[CH2:32][CH2:31][NH:30][CH2:29][C:28]=4[S:27][C:26]=3[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[Cl:20].CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:34]3[C:33]4[CH2:32][CH2:31][N:30]([C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][N:11]([CH:8]([CH3:10])[CH3:9])[CH3:12])[CH2:29][C:28]=4[S:27][C:26]=3[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[Cl:20]

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78485N-MethylisopropylamineHCID 81531DiisopropylethylamineHCID 841404-Bromo-2-butenoic acidHCID 58116912(3,4-Dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine

생성물 1

HCID 24748566N-(3,4-dichlorophenyl)-7-{(2E)-4-[isopropyl(methyl)amino]but-2-enoyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine수율 39.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 4-Bromo-but-2-enoic acid (638 mg, 3.87 mmol) in CH2Cl2 was added isopropylmethyamine (1.1 ml, 10.3 mmol), the mixture was stirred for 2 hours followed by addition of (3,4-dichloro-phenyl)-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)-amine (1.0 g, 2.57 mmol), EDCI (493 mg, 2.58 mmol), DIPEA (1.8 ml, 10.3 mmol). The resulting mixture was stirred at RT overnight. Solvents were removed and residue was purified by HPLC to gave the desired compound (500 mg, 13%). 1H-NMR (DMSO-d6) δ 8.46 (m, 1H), 8.39 (s, 1H), 7.88 (m, 1H), 7.62 (m, 1H), 7.42 (t, 1H), 6.67 (m, 1H), 3.94 (m, 2H), 3.87 (m, 4H), 2.75 (m, 2H), 2.11 (s, 3H), 0.96 (d, 6H); LCMS RT=2.72 min, [M+1]+=490.3.

후처리

  1. stirringThe resulting mixture was stirred at RT overnight
  2. customSolvents were removed
  3. customresidue was purified by HPLC

출처 및 근거

ORD 기록
ord-4b7faaaed7e54eaea9d67fe82f15a2f6
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501755B2

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