5-Chloro-2-methyl-1,8-naphthyridine → 4-[3-Chloro-5-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenoxymethyl]-N-methyl-benzamide

HRID 2197950Notes

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:15]=[C:16]([CH:29]=[C:30]([Cl:32])[CH:31]=1)[O:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([NH:25][CH3:26])=[O:24])=[CH:21][CH:20]=1>>[Cl:32][C:30]1[CH:29]=[C:16]([CH:15]=[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:31]=1)[O:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:25][CH3:26])=[O:24])=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridine

HCID 684587354-(3-Amino-5-chloro-phenoxymethyl)-N-methyl-benzamide

Product 1

HCID 684617794-[3-Chloro-5-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenoxymethyl]-N-methyl-benzamide

Procedure

The product from Example 1d (100 mg, 0.56 mmol) was reacted with the product from Example 195d (160 mg, 0.56 mmol) for 15 h following the procedure from Example 1g giving the crude title compound which was purified by trituration with EtOAc providing the product (240 mg, 99%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.75 (s, 3H), 2.79 (d, J=4.4 Hz, 3H), 5.26 (s, 2H), 6.90 (d, J=7.0 Hz, 1H), 7.14 (br-t, J=1.9 Hz, 1H), 7.18 (br-t, J=1.9 Hz, 1H), 7.20 (br-t, J=1.9 Hz, 1H), 7.53 (d, J=8.5 Hz, 2H), 7.77 (d, J=8.8 Hz, 1H), 7.87 (d, J=8.5 Hz, 2H), 8.47 (br-s, 1H), 8.50 (d, J=7.0 Hz, 1H), 9.08 (d, J=8.8 Hz, 1H), 11.08 (br-s, 1H); MS (ESI+) m/z 433, 435 (M+H)+, (ESI−) m/z 431, 433 (M−H)−.

Sources & evidence

ORD record: ord-a2b5630a638e4b41ad8efa1c67279432
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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