4-Chloro-1,8-naphthyridine → n-{4-[4-Methyl-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 2197739Notes

Reaction equation

HRID 2197739 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[S:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:23][CH:22]=1>>[CH3:19][C:17]1[CH:16]=[CH:15][C:14]([S:20][C:21]2[CH:22]=[CH:23][C:24]([NH:27][C:28](=[O:30])[CH3:29])=[CH:25][CH:26]=2)=[C:13]([NH:12][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 124225244-Chloro-1,8-naphthyridineHCID 43168935N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 68461211n-{4-[4-Methyl-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Procedure

The product from Example 16c (50 mg, 0.304 mmol) was reacted with the product from Example 18b (83 mg, 0.304 mmol) for 16 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (29 mg, 24%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.04 (s, 3H), 2.35 (s, 3H), 6.34 (d, J=6.99 Hz, 1H), 7.17 (d, J=7.72 Hz, 1H), 7.23 (d, J=8.46 Hz, 2H), 7.28-7.34 (m, 2H), 7.49 (d, J=8.82 Hz, 2H), 7.90 (dd, J=8.46, 4.41 Hz, 1H), 8.48 (d, J=6.99 Hz, 1H), 9.11 (dd, J=8.46, 1.47 Hz, 1H), 9.17 (dd, J=4.41, 1.47 Hz, 1H), 10.04 (s, 1H), 11.12 (s, 1H); MS (ESI+) m/z 401 (M+H)+, (ESI−) m/z 399 (M−H)−.

Sources & evidence

ORD record
ord-a05f82a7b60e4d8ea2aef57558e440ce
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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