4-Chloro-2,7-dimethyl-[1,8]naphthyridine → 4-[2-(2,7-Dimethyl-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenol

HRID 2197729Notes

Reaction equation

HRID 2197729 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[S:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1>>[CH3:13][C:4]1[CH:3]=[C:2]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2[S:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=1

Participants

3

Reactant 2

HCID 112063334-Chloro-2,7-dimethyl-[1,8]naphthyridineHCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 248979774-[2-(2,7-Dimethyl-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenol

Procedure

The product from Example 14b (60 mg, 0.31 mmol) was reacted with the product from Example 4c (72 mg, 0.31 mmol) for 12 h following the procedure from Example 1g giving the title compound as a crude solid which was purified by HPLC with TFA giving the product as a trifluoroacetic acid salt (45 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.23 (s, 3H) 2.75 (s, 3H) 3.43 (s, 3H) 6.10 (s, 1H) 6.68 (d, J=8.82 Hz, 2H) 6.99-7.20 (m, 3H) 7.20-7.38 (m, 2H) 7.75 (d, J=8.82 Hz, 1H) 8.96 (d, J=8.82 Hz, 1H) 9.86 (s, 1H) 10.78 (s, 1H) 14.21 (s, 1H); MS (APCI) m/z 386 (M−H)−.

Sources & evidence

ORD record
ord-f09ea205ac1e41f58124a6ed054e57ad
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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