5-Chloro-2-methyl-1,8-naphthyridine → HCID 68460663, compound

HRID 2358823Notes

Reaction equation

HRID 2358823 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:19]=[C:18]([CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>>[Br:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[O:21][CH2:20][C:18]1[CH:17]=[CH:16][C:15]([S:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridine2×HCID 66808364HCID 66808364, compound

Product 1

HCID 68460663HCID 68460663, compound

Conditions

Temperature
80 °C

Procedure

The product from Example 1d (0.034 g, 0.193 mmol) was reacted with the product from Example 225c (0.078 g, 0.193 mmol) for 15 h following the procedure from Example 1g. Consumption of starting material required a second addition of the product from Example 1d (0.019 g, 0.109 mmol) and continued heating at 80° C. (18 h). The crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.041 g, 32%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3 H) 5.15 (s, 2 H) 6.30 (d, J=7.35 Hz, 1 H) 6.79 (d, J=8.46 Hz, 2 H) 6.95-7.08 (m, 2 H) 7.16 (d, 1 H) 7.20-7.30 (m, 4 H) 7.45-7.55 (m, 2 H) 7.81 (d, J=8.82 Hz, 1 H) 8.47 (d, J=7.35 Hz, 1 H) 9.01 (d, J=8.46 Hz, 1 H) 9.98 (s, 1 H); Ms (ESI+) m/z 546.0 (M+H)+; (ESI−) m/z 542.0.

Workup

  1. customConsumption of starting material
  2. customThe crude title compound was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.041 g, 32%)

Sources & evidence

ORD record
ord-7909c4796ecd40c9ae48d798a4e7d181
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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