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p-Toluenesulfonic acid monohydrate → N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine

HRID 1842780
ノート
印刷プレビュー

反応式

HRID 1842780 の反応式
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[F:17][C:18]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:21]([NH2:22])=[C:20]([O:28][CH3:29])[CH:19]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)CCC>[F:17][C:18]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:21]([NH:22][C:2]2[N:7]=[C:6]([C:8]3[CH:9]=[N:10][N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=34)[CH:5]=[CH:4][N:3]=2)=[C:20]([O:28][CH3:29])[CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 574290724-Fluoro-2-methoxy-5-nitroaniline2 回HCID 866773443-(2-Chloropyrimidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine2 回

生成物 1

HCID 71240760N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine収率 37.5%

試薬・触媒・溶媒 1

HCID 22386
2-Pentanol
溶媒

反応条件

温度
85 °C

実験手順

A mixture of 3-(2-chloropyrimidin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (Intermediate 128, 3.6857 g, 15.70 mmol), 4-fluoro-2-methoxy-5-nitroaniline (Intermediate 23, 2.92 g, 15.70 mmol) and p-toluenesulfonic acid hydrate (3.29 g, 17.28 mmol) in 2-pentanol (100 mL) was stirred at 85° C. under an atmosphere of N2 for 1.5 h. The mixture was then concentrated in vacuo and the resulting reside was dissolved in CH2Cl2 (250 mL). This solution was washed with sat. NaHCO3 (2×100 mL), water (100 mL), and sat. brine (100 mL). The organic solution was concentrated in vacuo to give crude product. Purification by FCC, eluting with 0-10% CH3OH in CH2Cl2 provided an orange solid. This material was triturated with CH3OH to give a solid which was collected by filtration and dried in vacuo to give the title compound (2.26 g, 37%) as a yellow solid; 1H NMR: 1.75-1.86 (2H, m), 1.92-2.04 (2H, m), 3.09 (2H, t), 4.02 (3H, s), 4.12 (2H, t), 7.13 (1H, d), 7.35 (1H, d), 8.14 (1H, s), 8.25 (1H, s), 8.42 (1H, d), 9.02 (1H, d); m/z: ES+ MH+ 385.

後処理

  1. concentrationThe mixture was then concentrated in vacuo
  2. dissolutionthe resulting reside was dissolved in CH2Cl2 (250 mL)
  3. washThis solution was washed with sat. NaHCO3 (2×100 mL), water (100 mL), and sat. brine (100 mL)
  4. concentrationThe organic solution was concentrated in vacuo
  5. customto give crude product
  6. customPurification by FCC
  7. washeluting with 0-10% CH3OH in CH2Cl2
  8. customprovided an orange solid
  9. customThis material was triturated with CH3OH
  10. customto give a solid which
  11. filtrationwas collected by filtration
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-603d305fd23e49bea0991174bca978c6
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946235B2

反応ノート

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