4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 4-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide

HRID 2382071ノート

反応式

HRID 2382071 の反応式
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[N:3]=1.[CH2:16]([C:18]1[C:22]2=[N:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=[C:21]2[N:20]([NH2:31])[CH:19]=1)[CH3:17].C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[CH2:16]([C:18]1[C:22]2=[N:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=[C:21]2[N:20]([NH:31][C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:11]3[S:12][CH:13]=[CH:14][N:15]=3)=[N:5][CH:6]=2)=[O:10])[CH:19]=1)[CH3:17]

参加物

6

反応物 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 685536304-methyl-2-(2-thiazolyl)-5-Pyrimidinecarboxylic acidHCID 685552233-Ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-ylamine

生成物 1

HCID 591999754-Methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide収率 43.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 10340Sodium Carbonate溶媒

反応条件

温度
50 °C

実験手順

A solution of 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (88 mg, 0.40 mmol) and 3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-ylamine (89 mg, 0.40 mmol) in DMF (5 mL) is stirred at 50° C. for 1 h. The mixture is treated with DMTMM (113 mg, 0.41 mmol) and stirred at 50° C. overnight. The mixture is diluted with saturated aqueous Na2CO3 (5 mL) and stirred for 10 min. The precipitate is collected by filtration, washed with H2O (50 mL) and heptane (50 mL), and dried in vacuo to afford 4-methyl-2-thiazol-2-yl-pyrimidine-5-carboxylic acid (3-ethyl-5-trifluoromethyl-pyrrolo[3,2-b]pyridin-1-yl)-amide (75 mg, 40%). MS: 433 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 12.19 (s, NH, 1H), 9.28 (s, 1H), 8.15 (m, 2H), 8.08 (d, 1H), 7.87 (s, 1H), 7.72 (d, 1H), 2.83 (q, 2H), 2.77 (s, 3H), 1.35 (t, 3H).

後処理

  1. stirringstirred for 10 min
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with H2O (50 mL) and heptane (50 mL)
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-05d19c887b8f481192b643b8042e5a1b
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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