Chloroacetyl chloride → 2-chloro-N-(2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol-6-yl)-N-((pyridin-4-yl)methyl)acetamide

HRID 717798ノート

反応式

HRID 717798 の反応式
[CH3:1][N:2]1[CH2:22][CH2:21][C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH2:3]1)=[CH:11][CH:10]=[CH:9][C:8]=3[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.[Cl:30][CH2:31][C:32](Cl)=[O:33]>C(Cl)Cl>[Cl:30][CH2:31][C:32]([N:13]([C:8]1[C:7]2[NH:6][C:5]3[CH2:21][CH2:22][N:2]([CH3:1])[CH2:3][C:4]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)[CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[O:33]

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 673785662-methyl-N-(pyridin-4-ylmethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-6-amine

生成物 1

HCID 673791812-chloro-N-(2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol-6-yl)-N-((pyridin-4-yl)methyl)acetamide収率 189.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2,3,4,5-Tetrahydro-2-methyl-N-((pyridin-4-yl)methyl)-1H-pyrido[4,3-b]indol-6-amine (0.15 g, 0.515 mmol) was dissolved in DCM (10 mL) and cooled to 0° C. Triethylamine (0.145 mL, 1.03 mmol) was added dropwise with constant stirring. 2-Chloroacetylchloride (0.04 mL, 0.515 mmol) was added dropwise at the same temperature and, after addition, allowed to come to RT. The reaction mass was stirred at RT for 20 min. Ice water (3 mL) was then added and the mixture extracted with DCM. The organic layer was washed with saturated bicarbonate solution (3 mL) to obtain 2-chloro-N-(2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol-6-yl)-N-((pyridin-4-yl)methyl)acetamide (360 mg). The product (360 mg, 0.978 mmol) was dissolved in DMF (1 mL) and cooled to 0° C. Sodium hydride (46 mg, 1.173 mmol) was added and the reaction mixture was stirred at RT for 20 min. MeOH (2 mL) was added and concentrated under reduced pressure. The product was purified through reverse phase chromatography. Yield: 10.7 mg as freebase. 1H NMR (CD3OD, freebase) d (ppm): 8.45 (d, 2H), 7.40 (d, 2H), 7.10 (d, 1H), 6.90 (t, 1H), 6.56 (d, 1H), 5.30 (s, 2H), 5.06 (s, 2H), 4.0 (s, 2H), 3.20 (t, 2H), 3.0 (t, 2H), 2.76 (s, 3H).

後処理

  1. additionafter addition
  2. customto come to RT
  3. extractionthe mixture extracted with DCM
  4. washThe organic layer was washed with saturated bicarbonate solution (3 mL)

出典と根拠

ORDレコード
ord-459a143de8b4440c88c7fc03c11ff11a
出典データセット
uspto-grants-2015_11
特許番号
US09193728B2

反応ノート

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