5-Chloro-2-methyl-1,8-naphthyridine → HCID 68459178, compound

HRID 2358642Notes

Reaction equation

HRID 2358642 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.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[NH2:28]>>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[NH:28][C:2]1[C:3]2[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=2)[N:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 43349609HCID 43349609, compound

Product 1

HCID 68459178HCID 68459178, compound

Procedure

The product from Example 1d (200 mg, 1.12 mmol) was reacted with the product from Example 89b (260 mg, 1.12 mmol) for 72 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 (180 mg, 43%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.32 (s, 3H), 2.62 (s, 3H), 6.11 (br-s, 1H), 6.95-7.45 (m, 8H), 8.26 (br-s, 1H), 8.55-8.70 (m, 1H), 9.08 (br-s, 1H); MS (ESI+) m/z 376 (M+H)+, (ESI−) m/z 374 (M−H)−.

Sources & evidence

ORD record
ord-a0137a2fbb66425ebef4afc624e08408
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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