5-Chloro-2-methyl-1,8-naphthyridine → 4-(4-Methyl-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)phenol

HRID 2197839Notes

Reaction equation

HRID 2197839 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:27]=[C:26]([CH3:28])[CH:25]=[CH:24][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>>[CH3:28][C:26]1[CH:25]=[CH:24][C:15]([O:16][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=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:27]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 668083884-(2-Amino-4-methylphenoxy)phenol

Product 1

HCID 684592834-(4-Methyl-2-(7-methyl-1,8-naphthyridin-4-ylamino)phenoxy)phenol

Procedure

The product from Example 1d (278 mg, 1.56 mmol) was reacted with the product from Example 122b (336 mg, 1.56 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 (226 mg, 31%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.34 (s, 3H) 2.74 (s, 3H) 6.56 (d, J=6.99 Hz, 1H) 6.64-6.71 (m, 2H) 6.75-6.81 (m, 2H) 6.89 (d, J=8.46 Hz, 1H) 7.26 (dd, J=8.46, 1.84 Hz, 1H) 7.31 (s, 1H) 7.76 (d, J=8.82 Hz, 1H) 8.48 (d, J=6.99 Hz, 1H) 8.95 (d, J=8.46 Hz, 1H) 9.34 (s, 1H) 10.91 (s, 1H) 14.36 (s, 1H); MS (ESI+) m/z 358 (M+H−TFA)+.

Sources & evidence

ORD record
ord-3b171cda54d54203b3395361e3c53a9c
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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