Triethylamine → HCID 69252826, compound

HRID 409681Notes

Reaction equation

HRID 409681 reaction equation
CCCP(=O)=O.[CH3:7][NH:8][C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH:10]=1.[CH2:25]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[CH3:26].CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C.CCOC(C)=O>[CH2:25]([N:27]1[CH2:32][CH2:31][N:30]([C:20]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:11]3[CH:10]=[C:9]([NH:8][CH3:7])[N:14]=[CH:13][N:12]=3)=[CH:24][CH:23]=2)=[O:22])[CH2:29][CH2:28]1)[CH3:26]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 791961-EthylpiperazineHCID 16167369Propylphosphoric anhydrideHCID 69162548HCID 69162548, compound

Product 1

HCID 69252826HCID 69252826, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Propylphosphonic anhydride (50% in DMF, 2.72 mL, 4.7 mmol, 2 equiv) is added to a solution of 4-(6-methylamino-pyrimidin-4-ylamino)-benzoic acid (0.570 g, 2.33 mmol), N-ethyl-piperazine (0.33 mL, 2.57 mmol, 1.1 equiv), DMAP (7 mg), and Et3N (3.3 mL, 23.3 mmol, 10 equiv) in DMF (25 mL), at RT and under an argon atmosphere. The reaction mixture is stirred at RT for 1 h, diluted with EtOAc and washed with H2O. The aqueous layer is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM→DCM/2 N NH3 in MeOH, 86:14) to provide the title compound as a yellow foam: ES-MS: 341.2 [MH]+; tR=1.00 min (system 1); Rf=0.33 (CH2Cl2/2 N NH3 in MeOH, 9:1).

Workup

  1. washwashed with H2O
  2. extractionThe aqueous layer is extracted with EtOAc
  3. washThe combined organic phase is washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by silica gel column chromatography (DCM→DCM/2 N NH3 in MeOH, 86:14)

Sources & evidence

ORD record
ord-b639a771c2b041799caf3f8c9be00235
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

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