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

HRID 2358587Notes

Reaction equation

HRID 2358587 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-b5a955567a064bec9783c3b3ccac47b5
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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