4-Methylmorpholine → HCID 178448835, compound

HRID 1025486Notes

Reaction equation

HRID 1025486 reaction equation
[CH3:1][CH:2]([CH3:27])[CH2:3][NH:4][C:5]1[C:6]2[N:7]([C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.[NH:28]1[CH:32]=[CH:31][C:30]([NH2:33])=[N:29]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>>[CH3:1][CH:2]([CH3:27])[CH2:3][NH:4][C:5]1[C:6]2[N:7]([C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH:33][C:30]4[CH:31]=[CH:32][NH:28][N:29]=4)=[O:23])=[CH:20][CH:19]=3)=[CH:16][N:17]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 49800994HCID 49800994, compoundHCID 178418806HCID 178418806, compound

Product 1

HCID 178448835HCID 178448835, compoundYield 18%

Procedure

0.1 mmol 4-{4-[(2-methylpropyl)amino]imidazo[1,2-a]quinoxalin-1-yl}benzoic acid (1.0 mL, 0.1 M in NMP) (example 1.5), 0.2 mmol 1H-pyrazol-3-amine (1 mL, 0.5 M in NMP, 2 eq), 0.2 mmol HATU (1 mL, 0.5 M in NMP, 2 eq) and 0.4 mmol NMM (0.133 mL, 3 M in NMP, 4 eq) were combined, shaken at rt for 24 h and subjected to preparative HPLC to give 7.6 mg 4-{4-[(2-methylpropyl)amino]imidazo[1,2-a]quinoxalin-1-yl}-N-(1H-pyrazol-3-yl)benzamide (18%): UPLC-MS: RT=1.04 min; m/z (ES+) 426.5 [MH+]; required MW=425.5.

Sources & evidence

ORD record
ord-093aa74a1f9e4137be1e0c95479371af
Source dataset
uspto-grants-2014_05
Patent number
US08729082B2

Reaction notes

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