Water → HCID 86677348、化合物

HRID 1842823ノート

反応式

HRID 1842823 の反応式
[CH3:1][O:2][C:3]1[C:4]([NH:25][C:26]2[N:31]=[C:30]([C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]([CH3:41])[CH:33]=3)[CH:29]=[CH:28][N:27]=2)=[CH:5][C:6]([N+:22]([O-])=O)=[C:7]([N:9]([CH3:21])[CH2:10][CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=1.[NH4+].[Cl-].O>C(O)C.[Fe]>[NH2:22][C:6]1[CH:5]=[C:4]([NH:25][C:26]2[N:31]=[C:30]([C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[N:34]([CH3:41])[CH:33]=3)[CH:29]=[CH:28][N:27]=2)[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[N:9]([CH3:21])[CH2:10][CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17]

参加物

6

反応物 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 71269957HCID 71269957、化合物2 回

生成物 1

HCID 86677348HCID 86677348、化合物収率 94%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

tert-Butyl N-[2-[[5-methoxy-4-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-2-nitrophenyl]-methylamino]ethyl]-N-methylcarbamate (Intermediate 172, 428 mg, 0.76 mmol), iron (255 mg, 4.57 mmol) and NH4Cl (30.6 mg, 0.57 mmol) were heated in ethanol (16 mL) and water (5.33 mL) at reflux for 1.5 h (heating block at 100° C.) and then the mixture was cooled and concentrated in vacuo. The resulting residue was triturated in 10% CH3OH/CH2Cl2 (30 mL) and filtered. The residues were triturated again with 10% CH3OH/CH2Cl2 (30 mL) and filtered. The combined filtrates were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-5% CH3OH in CH2Cl2 gave the title compound (380 mg, 94%) as a light brown foam; 1H NMR: 1.41 (9H, s), 2.64 (3H, s), 2.80 (3H, s), 2.95 (2H, t), 3.34 (2H, t), 3.77 (3H, s), 3.89 (3H, s), 4.40 (2H, s), 6.78 (1H, s), 7.14-7.20 (2H, m), 7.23-7.27 (1H, m), 7.52 (1H, d), 7.55 (1H, s), 7.75 (1H, s), 8.28 (1H, d), 8.29 (1H, s), 8.42 (1H, d); m/z: ES+ MH+ 532.37.

後処理

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was triturated in 10% CH3OH/CH2Cl2 (30 mL)
  4. filtrationfiltered
  5. customThe residues were triturated again with 10% CH3OH/CH2Cl2 (30 mL)
  6. filtrationfiltered
  7. washThe combined filtrates were washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customPurification by FCC
  11. washeluting with 0-5% CH3OH in CH2Cl2

出典と根拠

ORDレコード
ord-f9cbbb4693924408943cc02a4581f9f7
出典データセット
uspto-grants-2015_02
特許番号
US08946235B2

反応ノート

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