1,2-Dichloroethane → (E)-3-(6-Aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indazol-3-ylmethyl)acrylamide

HRID 225913

반응식

HRID 225913 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][N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([CH2:27][NH:28][CH3:29])=[N:19]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:28]([CH3:29])[CH2:27][C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([CH3:17])[N:19]=2)=[O:16])=[CH:8][CH:7]=1

참가 물질

8

반응물 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7537473N-Methyl-N-[(1-methyl-1H-indazol-3-yl)methyl]amineHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acid

생성물 1

HCID 9797187(E)-3-(6-Aminopyridin-3-yl)-N-methyl-N-(1-methyl-1H-indazol-3-ylmethyl)acrylamide수율 74.1%

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), 1-methyl-3-(methylaminomethyl)-1H-indazole (210 mg, 1.2 mmole), HOBt.H2O (162 mg, 1.2 mmole), and Et3N (0.28 mL, 2.0 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 (238 mg, 74%) as a white foam: 1H NMR (400 MHz, CDCl3) δ 8.24 (m, 1 H), 7.90 (m, 1 H), 7.65 (m, 2 H), 7.35 (m, 2 H), 7.09 (m, 1 H), 6.73 (m, 1 H), 6.50 (m, 1 H), 5.04 (s, 2 H), 4.83 (bs, 2 H), 4.04 (s, 3 H), 3.10 (s, 3 H); MS (ES) m/e 322 (M+H)+.

후처리

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

출처 및 근거

ORD 기록
ord-61e84506eff941b28091198715f827c1
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557125B2

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