5-Chloro-2-methyl-1,8-naphthyridine → N-{4-[4-Benzyloxy-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 2358839Notes

Reaction equation

HRID 2358839 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]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:38])[CH3:37])=[CH:31][CH:30]=1>C(O)C>[CH2:21]([O:20][C:18]1[CH:17]=[CH:16][C:15]([S:28][C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:38])[CH3:37])=[CH:31][CH:30]=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)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68460688N-[4-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 68456648N-{4-[4-Benzyloxy-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Example 1d (30 mg, 0.17 mmol) was reacted in ethanol (1 mL) with the product from Example 233a (62 mg, 0.17 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 salt (24 mg, 47%). 1H NMR (300 MHz, DMSO-d6) ppm: 2.02 (s, 3 H) 2.75 (s, 3 H) 5.15 (s, 2 H) 6.29 (d, J=7.35 Hz, 1 H) 7.12 (d, J=8.82 Hz, 2 H) 7.16-7.27 (m, 2 H) 7.29-7.52 (m, 8 H) 7.78 (d, J=8.82 Hz, 1 H) 8.36 (d, J=6.99 Hz, 1 H) 8.94 (d, J=8.82 Hz, 1 H) 9.97 (s, 1 H) 11.00 (s, 1 H) 14.34 (s, 1 H); MS (ESI+) m/z 507 (M+H)+.

Sources & evidence

ORD record
ord-96e4fbc3a9b8487e9976c6a538dc7e99
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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