Ethanol → N-{4-[4-Methyl-2-([1,6]naphthyridin-5-ylamino)-phenylsulfanyl]-phenyl}-acetamide

HRID 883910Notes

Reaction equation

Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[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.C(O)C>>[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[N:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]3)[CH:18]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 122042345-Chloro-1,6-naphthyridine2×

HCID 43168935N-[4-(2-Amino-4-methyl-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 67249824N-{4-[4-Methyl-2-([1,6]naphthyridin-5-ylamino)-phenylsulfanyl]-phenyl}-acetamide

Conditions

Temperature: 100 °C

Procedure

The product from Example 36e (0.040 g, 0.24 mmol) was reacted with the product from Example 22b as a 1.5M solution in ethanol (0.162 mL, 0.24 mmol) for 17.5 h at 100° C. following the procedure from Example 7g. Consumption of starting material required a second addition of the product from Example 36e (0.027 g, 0.16 mmol) and continued heating at 100° C. (24 h) giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.038 g, 27%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.02 (s, 3 H) 2.36 (s, 3 H) 7.12-7.37 (m, 5 H) 7.38-7.53 (m, 3 H) 7.73-7.92 (m, J=8.64, 4.60 Hz, 2 H) 8.94 (d, J=8.46 Hz, 1 H) 9.18 (d, J=4.04 Hz, 1 H) 9.99 (s, 1 H); MS (ESI+) m/z 401.3 (M+H)+; (ESI−) m/z 399.0 (M−H)−.

Workup

customConsumption of starting material

Sources & evidence

ORD record: ord-0e251fb25a3340f28cf1e0ec89309680
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236950B2

Reaction notes

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