Water → HCID 59624816, compound

HRID 1943427Notes

Reaction equation

HRID 1943427 reaction equation
Br[C:2]1[C:3]2[N:4]([C:9]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[F:21])=[O:13])=[CH:10][N:11]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[Cl:8][C:6]1[CH:7]=[C:2]([NH:31][CH2:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)[C:3]2[N:4]([C:9]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[F:21])=[O:13])=[CH:10][N:11]=2)[N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 754524-MethoxybenzylamineHCID 81531DiisopropylethylamineHCID 596244958-Bromo-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 59624816HCID 59624816, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 8A (300 mg, 0.920 mmol) in NMP (2 mL) was added (4-methoxyphenyl)methanamine (0.120 mL, 0.920 mmol) and DIEA (0.161 mL, 0.920 mmol). The reaction mixture was stirred at 80° C. for 1 h, and then cooled to room temperature. Water was added. The light yellow solid was collected by filtration, rinsed with water and dried under vacuum to give 19A (348 mg, 89%). [M+H]=426. HPLC Peak Rt=3.000 minutes. (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 254 nm.)

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe light yellow solid was collected by filtration
  3. washrinsed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-c8f34bbcfc1a43d2a93c0d6b88012b8b
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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