5-METHYL-2-PHENOXYANILINE → HCID 68458104, compound

HRID 2197752Notes

Reaction equation

HRID 2197752 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:6]([NH2:8])[CH:7]=1.Cl[C:17]1[CH:26]=[CH:25][N:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][C:21]([CH3:27])=[N:22]2>>[CH3:27][C:21]1[N:22]=[C:23]2[C:18]([C:17]([NH:8][C:6]3[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=3[O:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:26][CH:25]=[N:24]2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 103978675-METHYL-2-PHENOXYANILINEHCID 122663725-Chloro-2-methyl-1,8-naphthyridine

Product 1

HCID 68458104HCID 68458104, compound

Procedure

The product from Example 41b (65 mg, 0.36 mmol) was reacted with the product from Example 1d following the procedure from Example 1g giving the tile compound that was triturated with ether giving the product as a hydrochloride salt (12 mg, 8.8%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.95 (t, J=7.73 Hz, 3H) 1.82 (q, J=7.72 Hz, 2H) 2.97 (dd, J=7.73 Hz, 2H) 6.68 (d, J=6.99 Hz, 1H) 6.99 (d, J=7.72 Hz, 2H) 7.12 (dd, J=8.82 Hz, 2H) 7.30 (dd, J=8.09 Hz, 2H) 7.66 (dd, J=8.82 Hz, J=2.58 Hz, 1H) 7.71 (d, J=2.2 Hz, 1H) 7.77 (d, J=8.82 Hz, 1H) 8.52 (d, J=6.98 Hz, 1H) 9.07 (d, J=8.82 Hz, 1H) 11.26 (br s, 1H) 14.45 (brs, 1H); MS (ESI+) m/z 390 (M−Cl)+; (ESI−) m/z 388 (M−HCl)−.

Workup

  1. customgiving the tile compound that
  2. customwas triturated with ether giving the product as a hydrochloride salt (12 mg, 8.8%)

Sources & evidence

ORD record
ord-227fcecd4e1845a0ae5e51113b5ca901
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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