4-Pyrimidinecarboxylic acid → HCID 66801975、化合物

HRID 528055

反応式

HRID 528055 の反応式
[NH2:1][C:2]1[C:3]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[NH:18][C:17]3=[O:25])[CH2:12][CH2:11]2)=[N:4][CH:5]=[N:6][C:7]=1[NH:8][CH3:9].CN(C(O[N:34]1N=N[C:36]2[CH:37]=[CH:38][CH:39]=[N:40][C:35]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C=CC(C(O)=O)=NC=1>CC(N(C)C)=O.C(N(C(C)C)CC)(C)C>[CH3:9][N:8]1[C:36]([C:37]2[CH:38]=[CH:39][N:40]=[CH:35][N:34]=2)=[N:1][C:2]2[C:7]1=[N:6][CH:5]=[N:4][C:3]=2[N:10]1[CH2:11][CH2:12][CH:13]([N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:17]2=[O:25])[CH2:14][CH2:15]1

参加物

6

反応物 3

HCID 1693064-Pyrimidinecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66802269HCID 66802269、化合物

生成物 1

HCID 66801975HCID 66801975、化合物収率 5%

試薬・触媒・溶媒 2

HCID 31374Dimethylacetamide溶媒HCID 81531Diisopropylethylamine溶媒

反応条件

温度
150 °C

実験手順

To a solution of 1-(1-(5-amino-6-(methylamino)pyrimidin-4-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (50 mg, 0.14 mmol) in anhydrous DMA (5 mL) and diisopropylethylamine (0.5 mL) were added HATU (150 mg, 0.39 mmol), and pyrimidine-4-carboxylic acid (100 mg, 0.8 mmol). The reaction mixture was stirred for 1 h, and concentrated under reduced pressure. The resulting oil was dissolved in 10 mL of dichloromethane, and the solution was washed with 5 mL of water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the residue was dissolved in Acetic acid (2 mL). The reaction mixture was heated in a microwave reactor to 150° C. for 20 min, and concentrated under reduced pressure. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 3 mg of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 10.85 (s, 1H), 9.34 (s, 1H), 8.96 (d, 1H), 8.36 (s, 1H), 8.27 (d, 1H), 7.21-7.14 (m, 1H), 6.93 (d, 3H), 4.64-4.52 (m, 1H), 4.18 (s, 3H), 2.37 (dd, 2H), 1.85 (t, 2H); MS (EI) for C23H21N9O: 428.4 (MH+).

後処理

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting oil was dissolved in 10 mL of dichloromethane
  3. washthe solution was washed with 5 mL of water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. dissolutionthe residue was dissolved in Acetic acid (2 mL)
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)

出典と根拠

ORDレコード
ord-aaf78d41a2c94ac181a12b073d4a929b
出典データセット
uspto-grants-2016_05
特許番号
US09346807B2

関連ノート

読み込み中…