5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461182, compound

HRID 2358822Notes

Reaction equation

HRID 2358822 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][C:25]([Br:28])=[CH:24][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:25]1[CH:26]=[CH:27][C:22]([O:21][CH2:20][C:18]2[CH:17]=[CH:16][C:15]([S:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)=[C:14]([NH:13][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:19]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridine2×HCID 68456180HCID 68456180, compound

Product 1

HCID 68461182HCID 68461182, compound

Conditions

Temperature
80 °C

Procedure

The product from Example 1d (0.03 g, 0.167 mmol) was reacted with the product from Example 223c (0.060 g, 0.15 mmol) for 17.5 h following the procedure from Example 1g. Consumption of starting material required a second addition of the product from Example 1d (0.016 g, 0.09 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 (0.056 g, 55%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3 H) 5.12 (s, 2 H) 6.30 (d, J=6.99 Hz, 1 H) 6.79 (d, J=8.82 Hz, 2 H) 6.92-7.08 (m, 3 H) 7.25 (d, J=8.82 Hz, 2 H) 7.42-7.54 (m, 4 H) 7.81 (d, J=8.82 Hz, 1 H) 8.47 (d, J=6.99 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)+.

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 (0.056 g, 55%)

Sources & evidence

ORD record
ord-b7d146f4f8424f63a478df019eac738b
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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