2-Pyridinemethanamine → HCID 46701256, compound

HRID 2090302Notes

Reaction equation

HRID 2090302 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([OH:26])=O)=[N:22][CH: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.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][NH2:41].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O.CO>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:18]4[CH:19]=[CH:20][C:21]([C:24]([NH:41][CH2:40][C:35]5[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=5)=[O:26])=[N:22][CH:23]=4)=[CH:13][CH:14]=3)[CH2:9]2)[CH:5]=[C:4]([N:27]2[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]2)[N:3]=1

Participants

7

Reactant 4

HCID 195092-PyridinemethanamineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59402358HCID 59402358, compound

Product 1

HCID 46701256HCID 46701256, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-{2-[2-amino-6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-1,2,3,4-tetrahydroisoquinolin-7-yl}pyridine-2-carboxylic acid (15 mg, 0.034 mmol) and 2-pyridinemethanamine (7.3 mg, 0.067 mmol, Aldrich, Cat. No. A65204) in N,N-dimethylformamide (1 mL) were added (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (21 mg, 0.040 mmol, NovaBiochem, Cat. 01-62-0016) and N,N-diisopropylethylamine (18 μL, 0.10 mmol). The resulting mixture was stirred at r.t. for two hours. Then the reaction solution was diluted in MeOH and purified by RP-HPLC (pH=10 system) to afford the desired compound. LCMS(M+H)+: m/z=536.4.

Workup

  1. custompurified by RP-HPLC (pH=10 system)

Sources & evidence

ORD record
ord-dfc74e39e991425bb331400464969442
Source dataset
uspto-grants-2013_05
Patent number
US08436008B2

Reaction notes

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