1,2-Dichloroethane → (E)-3-(6-Aminopyridin-3-yl)-N-methyl-N-(thieno[2,3-b]thiophen-2-ylmethyl)acrylamide

HRID 225916ノート

反応式

HRID 225916 の反応式
C(Cl)CCl.[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:8][CH:7]=1.[CH3:17][NH:18][CH2:19][C:20]1[S:27][C:23]2[S:24][CH:25]=[CH:26][C:22]=2[CH:21]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC>CN(C=O)C>[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:18]([CH3:17])[CH2:19][C:20]2[S:27][C:23]3[S:24][CH:25]=[CH:26][C:22]=3[CH:21]=2)=[O:16])=[CH:8][CH:7]=1

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 225937092-(Methylaminomethyl)thieno[2,3-b]thiophene

生成物 1

HCID 9797560(E)-3-(6-Aminopyridin-3-yl)-N-methyl-N-(thieno[2,3-b]thiophen-2-ylmethyl)acrylamide収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (230 mg, 1.2 mmole) was added to a solution (E)-3-(6-aminopyridin-3-yl)acrylic acid (164 mg, 1.0 mmole), 2-(methylaminomethyl)thieno[2,3-b]thiophene (220 mg, 1.2 mmole), HOBt.H2O (162 mg, 1.2 mmole), and Et3N (0.35 mL, 2.5 mmole) in dry DMF (5 mL) at RT. After 18 hr the mixture was concentrated. Flash chromatography on silica gel (5% EtOH/EtOAc) gave the title compound (138 mg, 42%) as a tan solid: 1H NMR (400 Hz, d6-DMSO) δ 8.15 (d, J=2.0 Hz, 1 H), 7.84 (bs, 1 H), 7.57 (d, J=5.2 Hz, 1 H), 7.43 (d, J=15.2 Hz, 1 H), 7.27 (m, 2 H), 6.44 (m, 2 H), 4.75 (s, 2 H), 3.13 (s, 3 H); for minor rotomer δ 5.00 (s, 2 H), 2.95 (s, 3 H); MS (ES) m/e 330 (M+H)+.

後処理

  1. customat RT
  2. concentrationAfter 18 hr the mixture was concentrated

出典と根拠

ORDレコード
ord-67ba59f8777a467582ea3736e80293ba
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

反応ノート

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