5-Chloro-2-methyl-1,8-naphthyridine → HCID 68458376, compound

HRID 2358630Notes

Reaction equation

HRID 2358630 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:24][CH:23]=2)=[C:18]([NH2:20])[CH:19]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:20][C:18]3[CH:19]=[C:14]([CH3:13])[CH:15]=[CH:16][C:17]=3[S:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[CH:24][CH:23]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 66808413HCID 66808413, compound

Product 1

HCID 68458376HCID 68458376, compound

Procedure

The product from Example 1d (50 mg, 0.28 mmol) was reacted with the product from Example 70a (86 mg, 0.28 mmol) for 24 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (64 mg, 50%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.37 (s, 3H), 2.73-2.79 (m, 3H), 6.30 (d, J=6.99 Hz, 1H), 6.78-6.87 (m, 2H), 6.97 (d, J=7.72 Hz, 2H), 7.17-7.24 (m, 1H), 7.24-7.28 (m, 2H), 7.32-7.36 (m, 3H), 7.37-7.46 (m, 2H), 7.79 (d, J=8.82 Hz, 1H), 8.42 (d, J=7.35 Hz, 1H), 8.96 (d, J=8.46 Hz, 1H), 11.00 (s, 1H); MS (ESI+) m/z 450 (M+H)+, (ESI−) m/z 448 (M−H)−.

Sources & evidence

ORD record
ord-67129e328a944788a7cda9e0a3cddd4c
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…