2-Amino-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide → 2-[3-(4-Chloro-3-methylphenyl)ureido]-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide

HRID 1483209

反応式

HRID 1483209 の反応式
[NH2:1][C:2]1[S:12][C:5]2[CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:13]([NH2:15])=[O:14].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][C:18]=1[CH3:26]>O1CCCC1.C(Cl)Cl>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:25])[NH:1][C:2]2[S:12][C:5]3[CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH2:9][C:4]=3[C:3]=2[C:13]([NH2:15])=[O:14])=[CH:19][C:18]=1[CH3:26]

参加物

5

反応物 2

HCID 6144392-Amino-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamideHCID 114009964-Chloro-3-methylphenyl isocyanate

生成物 1

HCID 1182701022-[3-(4-Chloro-3-methylphenyl)ureido]-6-ethyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxamide収率 38.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of compound F4 (450 mg, 2.00 mmol) in anhydrous tetrahydrofuran (10 mL) at room temperature under nitrogen was added a solution of compound F2 (402 mg, 2.40 mmol) in anhydrous methylene chloride (6 mL) dropwise over 3 min. Then the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered. The filter cake was washed with methylene chloride (5 mL) and then dried under reduced pressure to provide compound F5 as a white solid (301 mg, 38%): 1H NMR (300 MHz, DMSO-d6) δ 10.94 (s, 1H), 10.12 (s, 1H), 7.48-6.75 (m, 5H), 3.45 (s, 2H), 2.77 (d, J=4.8 Hz, 2H), 2.65 (d, J=4.8 Hz, 2H), 2.55-2.45 (m, 2H), 2.30 (s, 3H), 1.07 (t, J=6.6 Hz, 3H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. washThe filter cake was washed with methylene chloride (5 mL)
  3. customdried under reduced pressure

出典と根拠

ORDレコード
ord-a5b3254861cd4fd49089617374616ea5
出典データセット
uspto-grants-2016_08
特許番号
US09416141B2

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