2-Aminophenol → HCID 67330106, compound

HRID 2092599Notes

Reaction equation

HRID 2092599 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:35])=[C:8]([N:10]2[CH2:33][CH2:32][C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:16]=[CH:17][C:12]=3[C:11]2=[O:34])[CH:9]=1)=[C:2]=S.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[OH:43].CCN=C=NCCCN(C)C.Cl>C1COCC1>[O:43]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[N:36]=[C:2]1[NH:1][C:4]1[CH:5]=[CH:6][C:7]([CH3:35])=[C:8]([N:10]2[CH2:33][CH2:32][C:13]3[N:14]=[C:15]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([N:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:16]=[CH:17][C:12]=3[C:11]2=[O:34])[CH:9]=1

Participants

5

Reactant 3

HCID 58012-AminophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86675644HCID 86675644, compound

Product 1

HCID 67330106HCID 67330106, compoundYield 115.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(5-Isothiocyanato-2-methyl-phenyl)-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one (50.0 mg, 0.089 mmol), and 2-Amino-phenol (9.73 mg, 0.089 mmol) in THF (5 ml) was added EDC.HCl (25.6 mg, 0.133 mmol), and the reaction mixture was refluxed for 12 hour under nitrogen atmosphere. After 12 hrs, the reaction mass was concentrated to dryness to get crude compound. The crude obtained was subjected to preparative HPLC. The desired compound i.e., 6-[5-(Benzooxazol-2-ylamino)-2-methyl-phenyl]-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one was obtained as brown solid [54][Yield: 57.7 mg, 63.2%]

Workup

  1. temperaturethe reaction mixture was refluxed for 12 hour under nitrogen atmosphere
  2. concentrationthe reaction mass was concentrated to dryness
  3. customto get crude compound
  4. customThe crude obtained

Sources & evidence

ORD record
ord-83ed66d3e9cb49d7abca619c21f45859
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

Loading…