5-Chloro-2-methyl-1,8-naphthyridine → HCID 68456166, compound

HRID 2358825Notes

Reaction equation

HRID 2358825 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)=[C:6]([NH2:8])[CH:7]=1.Cl[C:17]1[CH:26]=[CH:25][N:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH3:27])=[N:22]2>>[CH3:27][C:21]1[N:22]=[C:23]2[C:18]([C:17]([NH:8][C:6]3[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=3[S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=3)=[CH:26][CH:25]=[N:24]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 43349617HCID 43349617, compound

Product 1

HCID 68456166HCID 68456166, compound

Procedure

The product of Example 227b (60 mg, 0.278 mmol) was reacted with the product from Example 1d (50 mg, 0.278 mmol) for 16 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 (24 mg, 28%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.44 (s, 3 H), 2.73 (s, 3 H), 6.45 (d, J=6.99 Hz, 1 H), 7.02-7.12 (m, J=7.72, 1.10 Hz, 2 H), 7.40-7.49 (m, 2 H), 7.50-7.58 (m, J=1.84 Hz, 1 H), 7.72 (dd, J=8.46, 3.31 Hz, 2 H), 8.21-8.27 (m, J=2.94, 0.74 Hz, 1 H), 8.38 (d, J=6.99 Hz, 1 H), 8.85 (d, J=8.82 Hz, 1 H), 10.99 (s, 1 H); MS (ESI+) m/z 359 (M+H−TFA)+; (ESI−) m/z 357 (M−H−TFA)−.

Sources & evidence

ORD record
ord-c2ac6f58b0774ade8262e1cb8e350adb
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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