2-Amino-5-methylpyridine → HCID 59212266, compound

HRID 424715Notes

Reaction equation

HRID 424715 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16](O)=[O:17])[C:3]1=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:48][C:49]1[CH:50]=[CH:51][C:52]([NH2:55])=[N:53][CH:54]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([NH:55][C:52]2[CH:51]=[CH:50][C:49]([CH3:48])=[CH:54][N:53]=2)=[O:17])[C:3]1=[O:23]

Participants

6

Reactant 4

HCID 153482-Amino-5-methylpyridineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59212472HCID 59212472, compound

Product 1

HCID 59212266HCID 59212266, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylbenzoic acid 29 (50 mg, 0.17 mmol) in DMF (1 mL) is treated with HATU (97 mg, 0.255 mmol), 5-methylpyridin-2-amine (22 mg, 0.2 mmol) and DIPEA (0.089 mL, 0.51 mmol) at 80° C. for 2 h. The residue is purified by preparative LC/MS to give the desired product M6 as an off-white solid. 1H NMR (400 MHz, MeOH-d4) δ 9.12 (s, 1H), 8.26 (m, 1H), 8.22 (d, J=8.7 Hz, 1H), 8.16 (s, 1H), 8.07 (dd, J=8, 1.6 Hz, 1H), 8.02 (s, 1H), 7.94 (s, 1H), 7.86 (m, 1H), 7.57 (d, J=8 Hz, 1H), 3.85 (s, 3H), 2.87 (s, 3H), 2.46 (s, 3H), 2.35 (s, 3H); LC/MS (M+1, m/z): 399.2.

Workup

  1. customThe residue is purified by preparative LC/MS

Sources & evidence

ORD record
ord-770c05d92f6a44b99637ec38186980af
Source dataset
uspto-grants-2012_01
Patent number
US08106068B2

Reaction notes

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