5-Chloro-2-methyl-1,8-naphthyridine → HCID 67248596, compound

HRID 2358644Notes

Reaction equation

HRID 2358644 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.[NH2:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[S:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:13][C:14]3[CH:15]=[C:16]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH:26]=[CH:27][C:28]=3[S:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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 67249752HCID 67249752, compound

Product 1

HCID 67248596HCID 67248596, compound

Procedure

The product from Example 1d (557 mg, 3.12 mmol) was reacted with the product from Example 90b (1.032 mg, 3.12 mmol) for 18 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 (310 mg, 17%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.37 (s, 9H) 2.76 (s, 3H) 4.19 (d, J=6.25 Hz, 2H) 6.29 (d, J=6.99 Hz, 1H) 7.25 (s, 5H) 7.31 (s, 1H) 7.37 (d, J=3.31 Hz, 2H) 7.44-7.56 (m, 1H) 7.79 (d, J=8.82 Hz, 1H) 8.42 (d, J=6.99 Hz, 1H) 8.94 (d, J=8.46 Hz, 1H) 11.05 (s, 1H) 14.43 (s, 1H); MS (ESI+) m/z 473 (M+H)+.

Sources & evidence

ORD record
ord-604a029843a14d6cafedb163eaacc14f
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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