Triethylamine → 4-(4-Methylpiperazin-1-yl)-6-{2-[(6-pyrrolidin-1-ylpyridin-3-yl)acetyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}pyrimidin-2-amine

HRID 449468Notes

Reaction equation

HRID 449468 reaction equation
Cl.Cl.Cl.[CH3:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[C:15]([C:17]3[CH:26]=[C:25]4[C:20]([CH2:21][CH2:22][NH:23][CH2:24]4)=[CH:19][CH:18]=3)[N:14]=[C:13]([NH2:27])[N:12]=2)[CH2:7][CH2:6]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[N:62]1([C:67]2[N:72]=[CH:71][C:70]([CH2:73][C:74](O)=[O:75])=[CH:69][CH:68]=2)[CH2:66][CH2:65][CH2:64][CH2:63]1>>[CH3:4][N:5]1[CH2:6][CH2:7][N:8]([C:11]2[CH:16]=[C:15]([C:17]3[CH:26]=[C:25]4[C:20]([CH2:21][CH2:22][N:23]([C:74](=[O:75])[CH2:73][C:70]5[CH:71]=[N:72][C:67]([N:62]6[CH2:63][CH2:64][CH2:65][CH2:66]6)=[CH:68][CH:69]=5)[CH2:24]4)=[CH:19][CH:18]=3)[N:14]=[C:13]([NH2:27])[N:12]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178485582-(6-(Pyrrolidin-1-yl)pyridin-3-yl)acetic acidHCID 675428394-(4-Methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine trihydrochloride

Product 1

HCID 497793744-(4-Methylpiperazin-1-yl)-6-{2-[(6-pyrrolidin-1-ylpyridin-3-yl)acetyl]-1,2,3,4-tetrahydroisoquinolin-7-yl}pyrimidin-2-amine

Procedure

4-(4-methylpiperazin-1-yl)-6-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrimidin-2-amine trihydrochloride (180 mg, 0.43 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (190 mg, 0.43 mmol) and triethylamine (0.30 mL, 2.1 mmol) were added to 2-(6-(pyrrolidin-1-yl)pyridin-3-yl)acetic acid (0.4 mmol, from the above step) in N,N-dimethylformate (5 mL). The reaction mixture was stirred at r.t. for 2 h. The mixture was purified by Prep-LCMS (pH=10) to afford the desired product. Analytic LCMS (M+H)+: m/z=513.2.

Workup

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

Sources & evidence

ORD record
ord-b2b73613086f4b2ca9940e6b4a77a87a
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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