Aniline → HCID 24956698, compound

HRID 424717Notes

Reaction equation

HRID 424717 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:16]([N:18]=[C:19]=[O:20])=[O:17])[C:3]1=[O:25].[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([CH3:12])[CH:10]=2)[CH:5]=[C:4]([C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:16]([NH:18][C:19](=[O:20])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:17])[C:3]1=[O:25]

Participants

4

Reactant 2

HCID 6115AnilineHCID 59212307HCID 59212307, compound

Product 1

HCID 24956698HCID 24956698, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1,7-Dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylbenzoyl isocyanate 31 (10 mg, 0.03 mmol) is suspended in DCM at rt with aniline (3 mg, 0.3 mmol) for 1 h. Solvent is removed and the residue is purified by preparative LC/MS to give the desired product N1. 1H NMR (400 MHz, DMSO-d6) δ 11 (s, 1H), 10.8 (s, 1H), 8.99 (s, 1H), 8.1 (s, 1H), 8.01 (d, J=8 Hz, 1H), 7.95 (s, 1H), 7.69 (s, 1H), 7.59 (s, 1H), 7.57 (s, 1H), 7.48 (d, J=7.9 Hz, 1H), 7.36 (m, 2H), 7.12 (t, J=7 Hz, 1H), 2.7 (s, 3H), 2.51 (s, 3H), 2.25 (s, 3H); LC/MS (M+1, m/z): 427.2.

Workup

  1. customSolvent is removed
  2. customthe residue is purified by preparative LC/MS

Sources & evidence

ORD record
ord-4990619e26834549a22007ccf0a2accf
Source dataset
uspto-grants-2012_01
Patent number
US08106068B2

Reaction notes

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