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4-Methylmorpholine → HCID 58296303, compound

HRID 390065
Notes
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Reaction equation

HRID 390065 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:7]=[C:8]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)[C:9]2[C:15](=[O:16])[NH:14][CH:13]=[CH:12][C:10]=2[N:11]=1.[CH3:25][C:26]([O:29][C:30]([N:32]([CH3:37])[CH2:33][C:34](O)=[O:35])=[O:31])([CH3:28])[CH3:27].O.N1(O)C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:37][N:32]([CH2:33][C:34]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[N:7]=[C:8]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)[C:9]2[C:15](=[O:16])[NH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:35])[C:30](=[O:31])[O:29][C:26]([CH3:28])([CH3:25])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 44818005HCID 44818005, compound

Product 1

HCID 58296303
HCID 58296303, compound
Yield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(3-aminopropyl)amino]-4-[(3-methylphenyl)amino]pyrido[4,3-d]pyrimidin-5(6H)-one (50 mg, 0.114 mmol) in N,N-Dimethylformamide (DMF) (1.5 mL) were added N-{[(1,1-dimethylethyl)oxy]carbonyl}-N-methylglycine (25.9 mg, 0.137 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (34.9 mg, 0.228 mmol), 4-methylmorpholine (57.7 mg, 0.570 mmol), and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (28.4 mg, 0.148 mmol), and the reaction mixture was stirred for 2.5 h. It was then concentrated and the residue was subjected to reverse-phase HPLC purification to give 33 mg of the title compound.

Workup

  1. concentrationIt was then concentrated
  2. customthe residue was subjected to reverse-phase HPLC purification

Sources & evidence

ORD record
ord-f40902b7d82249089a00fea9219d6e95
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08383635B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes