Ammonium Chloride → 4-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-N'-(4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)benzene-1,3-diamine

HRID 1842803노트

반응식

HRID 1842803 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH:14]=2)[C:6]([N+:16]([O-])=O)=[CH:5][C:4]=1[NH:19][C:20]1[N:25]=[C:24]([C:26]2[CH:27]=[N:28][N:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=23)[CH:23]=[CH:22][N:21]=1.[NH4+].[Cl-]>[Fe].O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH:14]=2)[C:6]([NH2:16])=[CH:5][C:4]=1[NH:19][C:20]1[N:25]=[C:24]([C:26]2[CH:27]=[N:28][N:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=23)[CH:23]=[CH:22][N:21]=1

참가 물질

5

반응물 2

HCID 25517Ammonium Chloride2회HCID 71240769HCID 71240769, 화합물2회

생성물 1

HCID 866773074-methoxy-6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-N'-(4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-yl)benzene-1,3-diamine수율 76.4%

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 962Water용매

실험 절차

A mixture of N-[2-methoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-5-nitrophenyl]-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine (Intermediate 151, 285 mg, 0.56 mmol), iron (188 mg, 3.36 mmol), NH4Cl (21 mg, 0.39 mmol) ethanol (10.5 mL) and water (3.5 mL) was heated at reflux for 1.5 h. The reaction was judged to be incomplete so further NH4Cl (21 mg, 0.39 mmol) and iron (188 mg, 3.36 mmol) were added and the mixture was heated at reflux for a further 1.5 h. After cooling, the mixture was filtered and concentrated in vacuo. Purification by FCC, eluting with 2-10% 7N methanolic ammonia in CH2Cl2 gave the title compound (183 mg, 69%) as an orange gum which was used without further purification; 1H NMR: 2.30 (3H, s), 2.36-2.45 (2H, m), 2.60 (2H, t), 2.98-3.06 (2H, m), 3.74 (3H, s), 4.34 (2H, s), 5.73 (1H, s), 6.64 (1H, s), 7.09 (1H, m), 7.26 (1H, d), 7.38-7.49 (2H, m), 8.00 (1H, s), 8.35 (1H, d), 8.58 (1H, d), 8.80 (2H, m); m/z: ES+ MH+ 427.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. additionwere added
  4. temperaturethe mixture was heated
  5. temperatureat reflux for a further 1.5 h
  6. temperatureAfter cooling
  7. filtrationthe mixture was filtered
  8. concentrationconcentrated in vacuo
  9. customPurification by FCC
  10. washeluting with 2-10% 7N methanolic ammonia in CH2Cl2

출처 및 근거

ORD 기록
ord-a2fb77aa3d43496082f4b88e8cb14c63
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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