Methylamine → HCID 70818069, compound

HRID 1501367Notes

Reaction equation

HRID 1501367 reaction equation
[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[N:16][N:15]4[C:23]=3[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.CN.C1C[N:35]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:34]C1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[NH2:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[CH:18][C:17]([C:20]([NH:35][CH3:34])=[O:22])=[N:16][N:15]4[C:23]=3[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 70817834HCID 70817834, compound

Product 1

HCID 70818069HCID 70818069, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[4-(1-aminocyclobutyl)phenyl]-3-phenylimidazo[1,2-b]pyridazine-6-carboxylic acid that was prepared in a manner analgous to that described for Example 8 (0.15 g, 0.39 mmol) and methylamine (2 M in THF, 1.43 mL, 2.93 mmol, 7.5 equiv) in DMF (1 mL) was added PYBOP (0.22 g, 0.43 mmol 1.10 equiv) and N,N-diisopropylethylamine (0.27 mL, 1.56 mmol, 4.0 equiv). The resulting mixture was stirred at room temperature for 25 h, then was treated with water (10 mL). The resulting aqueous mixture was extracted with EtOAc (4×15 mL). The combined organic phases were washed with water (2×15 mL), dried (Na2SO4 anh.) and concentrated under reduced pressure. The resulting material was triturated with MeOH to give 2-[4-(1-aminocyclobutyl)phenyl]-N-methyl-3-phenylimidazo[1,2-b]pyridazine-6-carboxamide (0.085 g, 55%):

Workup

  1. extractionThe resulting aqueous mixture was extracted with EtOAc (4×15 mL)
  2. washThe combined organic phases were washed with water (2×15 mL)
  3. dry with materialdried (Na2SO4 anh.)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting material was triturated with MeOH

Sources & evidence

ORD record
ord-3d51a92ea57047769b8f02aff4713f74
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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