Diisopropylethylamine → HCID 178463575, compound

HRID 473415Notes

Reaction equation

HRID 473415 reaction equation
[C:1]1([C:7]2[C:8]([CH:17]([NH2:19])[CH3:18])=[N:9][C:10]3[C:15]([CH:16]=2)=[N:14][CH:13]=[CH:12][CH:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:21]12[N:29]=[CH:28][N:27]=[C:26]1[C:25](Cl)=[N:24][CH:23]=[N:22]2.CCN(C(C)C)C(C)C>CCCCO>[C:1]1([C:7]2[C:8]([CH:17]([NH:19][C:25]3[N:24]=[CH:23][N:22]=[C:21]4[C:26]=3[N:27]=[CH:28][NH:29]4)[CH3:18])=[N:9][C:10]3[C:15]([CH:16]=2)=[N:14][CH:13]=[CH:12][CH:11]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22135701HCID 22135701, compoundHCID 58318606HCID 58318606, compound

Product 1

HCID 178463575HCID 178463575, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1-(3-Phenyl-1,5-naphthyridin-2-yl)ethanamine (46 mg, 0.19 mmol), 4-amino-6-chloropurine (28.5 mg, 1.0 eq) and hunig's base (39 μL, 1.2 eq) in n-BuOH (2 mL) was heated to 130° C. overnight. The mixture was cooled to rt, concentrated, and purified by reverse phase HPLC (MeCN/H2O/0.1% TFA, 10% to 60%) to give a white powder (50 mg) as TFA salt. 1H NMR (400 MHz, CD3OD) δ ppm 9.05 (1H, d, J=4.0 Hz), 8.65 (1H, d, J=8.0 Hz), 8.50-8.47 (2H, m), 8.29 (1H, s), 7.90 (1H, dd, J=8.0, 4.0 Hz), 7.62-7.47 (5H, m), 6.12-6.01 (1H, m), 1.63 (3H, d, J=8.0 Hz); LC-MS (ESI) m/z 368 [M+H]+.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase HPLC (MeCN/H2O/0.1% TFA, 10% to 60%)

Sources & evidence

ORD record
ord-25ff3c473dc44d129c5dc3881d7ebd26
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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