Methylamine → HCID 59496676, compound

HRID 449330Notes

Reaction equation

HRID 449330 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][N:15]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([OH:27])=O)=[N:23][CH:24]=4)[CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[C:5]([N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[N:4]=1.CN.F[P-](F)(F)(F)(F)F.[N:44]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:48]2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[NH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][N:15]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:44][CH3:48])=[O:27])=[N:23][CH:24]=4)[CH2:16]3)=[CH:11][CH:10]=2)[CH:6]=[C:5]([N:28]2[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]2)[N:4]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67541538HCID 67541538, compound

Product 1

HCID 59496676HCID 59496676, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-{7-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3,4-dihydroisoquinolin-2(1H)-yl}pyridine-2-carboxylic acid HCl salt (16.4 mg, 0.0296 mmol), methylamine (0.018 ml, 0.036 mmol) (2.0 M solution in THF), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (14.4 mg, 0.0326 mmol) and 4-methylmorpholine (16.3 uL, 0.148 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at r.t. overnight. The mixture was purified by RP-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=459.4.

Workup

  1. customThe mixture was purified by RP-LCMS (pH=10)

Sources & evidence

ORD record
ord-74e40fa249104cd8a3f0df39861ba702
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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