Methylamine → HCID 59402301, compound

HRID 2090477Notes

Reaction equation

HRID 2090477 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[S:20][C:21]([C:24]([OH:26])=O)=[CH:22][N:23]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[N:3]=1.F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2C=CC=CC=2N=N1.CN.O1CCCC1>CN(C=O)C.CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH:17]([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:19]4[S:20][C:21]([C:24]([NH:41][CH3:45])=[O:26])=[CH:22][N:23]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)[N:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59402253HCID 59402253, compound

Product 1

HCID 59402301HCID 59402301, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-3-methyl-1,2,3,4-tetrahydroisoquinolin-7-yl}-1,3-thiazole-5-carboxylic acid (15.0 mg, 0.0322 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (14.2 mg, 0.0322 mmol) and 2.0 M of methylamine in tetrahydrofuran (0.100 mL, 0.200 mmol) in DMF (1.0 mL) was stirred at r.t. for 2 h., and was diluted with methanol (0.8 mL). The resulting solution was purified by RP-HPLC (pH=10) to afford the desired product. LCMS (M+H)+: m/z=479.1.

Workup

  1. customThe resulting solution was purified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-dff5bc6c80514dcaa00fb99f9a9aa509
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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