Water → HCID 86677348, 화합물

HRID 1842823노트

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HRID 1842823 반응식
[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]

참가 물질

6

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 71269957HCID 71269957, 화합물2회

생성물 1

HCID 86677348HCID 86677348, 화합물수율 94%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f9cbbb4693924408943cc02a4581f9f7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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