HCID 59624544, compound → HCID 178511619, compound

HRID 1943465Notes

Reaction equation

HRID 1943465 reaction equation
[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

Participants

4

Reactant 2

HCID 59624544HCID 59624544, compoundHCID 178511674HCID 178511674, compound

Product 1

HCID 178511619HCID 178511619, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-58c8c8da6cf8486b80c3ac25b54b1320
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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