4-Methylmorpholine → HCID 86595017, compound

HRID 1634568Notes

Reaction equation

HRID 1634568 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 ), 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 ), 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-db1ea0e83d56479b8c68c69e4d74fd50
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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