4-Methylmorpholine → HCID 86595017, compound

HRID 1792282Notes

Reaction equation

HRID 1792282 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:10]2=[N:11][N:12]([CH3:22])[C:13]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])=[C:9]2[N:8]=[C:7]([CH3:23])[N:6]=1.CN1CC[O:28]CC1.[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37](CC(O)=O)=[CH:36][C:35]=1[O:44][CH3:45])[CH3:32].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>CN(C)C(=O)C.CCOC(C)=O>[Cl:20][C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:21])[C:14]=1[C:13]1[N:12]([CH3:22])[N:11]=[C:10]2[C:9]=1[N:8]=[C:7]([CH3:23])[N:6]=[C:5]2[NH:4][CH:3]([C:37]1[CH:38]=[CH:39][C:34]([O:33][CH2:31][CH3:32])=[C:35]([O:44][CH3:45])[CH:36]=1)[C:2]([NH2:1])=[O:28]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 671124-Ethoxy-3-methoxyphenylacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 22034136HCID 22034136, compound

Product 1

HCID 86595017HCID 86595017, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of (2-aminoethyl)[3-(2,6-dichlorophenyl)-2,5-dimethylpyrazolo[3,4-e]pyrimidin-7-yl]amine (175 mg, 0.5 mmol) in N,N-dimethylacetamide (5 mL), add 4-methylmorpholine (101 mg, 1.0 mmol), 2-(4-ethoxy-3-methoxyphenyl)acetic acid (115 mg, 0.55 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (331 mg, 0.75 mmol). Stir the reaction mixture at ambient temperature for 14 h and dilute with EtOAc (15 mL). Wash the organic extracts successively with water (10 mL), brine (10 mL), saturated NH4Cl (10 mL), 2N NaOH (10 mL), brine (10 mL), dry over MgSO4 and evaporate under reduced pressure to obtain the title compound.

Workup

  1. washWash the organic extracts successively with water (10 mL), brine (10 mL), saturated NH4Cl (10 mL), 2N NaOH (10 mL), brine (10 mL)
  2. dry with materialdry over MgSO4
  3. customevaporate under reduced pressure

Sources & evidence

ORD record
ord-1b888f0018af40c7a2290f4c72bf12da
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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