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

HRID 1710566노트

반응식

HRID 1710566 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 MHz, d6-DMSO) δ 8.15 (d, J=2.0 Hz, 1H), 7.84 (bs, 1H), 7.57 (d, J=5.2 Hz, 1H), 7.43 (d, J=15.2 Hz, 1H), 7.27 (m, 2H), 6.44 (m, 2H), 4.75 (s, 2H), 3.13 (s, 3H); for minor rotomer δ 5.00 (s, 2H), 2.95 (s, 3H); MS (ES) m/e 330 (M+H)+.

후처리

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

출처 및 근거

ORD 기록
ord-63f992e6341641279e2412e5cc591c56
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790716B2

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