2-Aminophenol → HCID 67330106, compound

HRID 1853965Notes

Reaction equation

HRID 1853965 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 clear solution of 6-(5-Amino-2-methyl-phenyl)-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one (75 mg, 0.169 mmol) in the DCM (5 ml) was added Di(2-pyridyl)thionocarbonate (47 mg, 0.203 mmol) all at once, and the reaction mixture was allowed to stirred for 3 hours at room temperature. After 3 hours, the reaction mixture was diluted with water, extracted with ethyl acetate. The organic layer was given a brine wash, dried over sodium sulphate and concentrated to dryness to get sticky mass which was given a hexane wash to get 70.3 mg 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 [53] [Yield: 85.6%] as light brown coloured. 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-38c8ed41a8e34c1e952a0c0ef47b6a61
Source dataset
uspto-grants-2015_02
Patent number
US08962637B2

Reaction notes

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