HCID 59624544, 화합물 → HCID 178511619, 화합물

HRID 1943465노트

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HRID 1943465 반응식
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=[C:13](Cl)[CH:14]=2)[CH:5]=[CH:4][CH:3]=1.[C@H:29]1([NH2:36])[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31][CH2:30]1>CN1C(=O)CCC1>[NH2:35][C@H:32]1[CH2:33][CH2:34][C@H:29]([NH:36][C:13]2[CH:14]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=3)[C:10]3[N:11]([C:16]([C:19]([NH:21][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][C:23]=4[F:28])=[O:20])=[CH:17][N:18]=3)[N:12]=2)[CH2:30][CH2:31]1

참가 물질

4

반응물 2

HCID 59624544HCID 59624544, 화합물HCID 178511674HCID 178511674, 화합물

생성물 1

HCID 178511619HCID 178511619, 화합물수율 71%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
100 °C

실험 절차

A mixture of 8-(6-bromopyridin-2-ylamino)-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide (550 mg, 1.189 mmol) and (trans)-cyclohexane-1,4-diamine (1086 mg, 9.51 mmol) in NMP (4 mL) was heated at 100° C. overnight. The reaction mixture was cooled to room temperature and poured onto ice. The resulting yellow solid was collected by filtration and rinsed with water. The still wet solid pad was concentrated from DCM/MeOH 3 times until dryness. The solid residue was treated with a small amount of MeOH, and the yellow solid was collected by filtration and dried under vacuum to give the title compound (456 mg, 71%). HPLC Rt=2.870 min (Chromolith SpeedROD 4.6×50 mm, 10-90% aqueous methanol containing 0.1% TFA, 4 min gradient, monitored at 220 nm), [M+H]=542.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. additionpoured onto ice
  3. filtrationThe resulting yellow solid was collected by filtration
  4. washrinsed with water
  5. concentrationThe still wet solid pad was concentrated from DCM/MeOH 3 times until dryness
  6. additionThe solid residue was treated with a small amount of MeOH
  7. filtrationthe yellow solid was collected by filtration
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-58c8c8da6cf8486b80c3ac25b54b1320
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389527B2

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