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 1887427ノート

反応式

HRID 1887427 の反応式
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]

参加物

7

反応物 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

生成物 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-amine収率 39.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-4b7faaaed7e54eaea9d67fe82f15a2f6
出典データセット
uspto-grants-2013_08
特許番号
US08501755B2

反応ノート

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