Water → N1-(2-dimethylaminoethyl)-N4-[4-(1H-indol-3-yl)pyrimidin-2-yl]-5-methoxy-N1-methylbenzene-1,2,4-triamine

HRID 1842820노트

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HRID 1842820 반응식
O.[CH3:2][N:3]([CH3:35])[CH2:4][CH2:5][N:6]([CH3:34])[C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][C:10]([NH:16][C:17]2[N:22]=[C:21]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=2)=[C:9]([O:32][CH3:33])[CH:8]=1.[NH4+].[Cl-]>[Fe].C(O)C>[CH3:35][N:3]([CH3:2])[CH2:4][CH2:5][N:6]([CH3:34])[C:7]1[C:12]([NH2:13])=[CH:11][C:10]([NH:16][C:17]2[N:22]=[C:21]([C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH:20]=[CH:19][N:18]=2)=[C:9]([O:32][CH3:33])[CH:8]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 71240878N1-(4-(1H-indol-3-yl)pyrimidin-2-yl)-N4-(2-(dimethylamino)ethyl)-2-methoxy-N4-methyl-5-nitrobenzene-1,4-diamine2회

생성물 1

HCID 86677322N1-(2-dimethylaminoethyl)-N4-[4-(1H-indol-3-yl)pyrimidin-2-yl]-5-methoxy-N1-methylbenzene-1,2,4-triamine수율 97%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

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온도
105 °C

실험 절차

Water (4 mL) was added in one portion to a mixture of N′-(2-dimethylaminoethyl)-N-[4-(1H-indol-3-yl)pyrimidin-2-yl]-2-methoxy-N′-methyl-5-nitrobenzene-1,4-diamine (Intermediate 169, 270 mg, 0.59 mmol), iron (196 mg, 3.51 mmol), NH4Cl (21.9 mg, 0.41 mmol) and ethanol (24 mL). The resulting mixture was heated at 105° C. for 3 h then filtered through diatomaceous earth (Celite™). The filtrate was concentrated in vacuo and then part-purified by ion exchange chromatography, using an SCX column and eluting with 0.35M methanolic ammonia. Appropriate fractions were combined and concentrated in vacuo to give the title compound (244 mg, 97%) as a brown solid which was used without further purification; 1H NMR: 2.18 (6H, s), 2.37 (2H, s), 2.64 (3H, s), 2.90 (2H, s), 3.76 (3H, s), 6.77 (1H, s), 7.03-7.26 (3H, m), 7.46 (1H, d), 7.52 (1H, s), 7.74 (1H, s), 8.18-8.35 (2H, m), 8.42 (1H, d), 11.72 (1H, s); m/z: ES+ MH+ 432.

후처리

  1. filtrationthen filtered through diatomaceous earth (Celite™)
  2. concentrationThe filtrate was concentrated in vacuo
  3. custompart-purified by ion exchange chromatography
  4. washeluting with 0.35M methanolic ammonia
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f952effef33245baad8aac300087ba72
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946235B2

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