1,2-Dichloroethane → HCID 57632944, compound

HRID 1870057Notes

Reaction equation

HRID 1870057 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C(Cl)CCl.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[N:20][C:21]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([OH:35])=O)=[CH:27][CH:26]=3)=[N:22][CH:23]=2)=[CH:14][CH:13]=1.[NH4+].[Cl-]>CN(C1C=CN=CC=1)C.ClCCl.CN1C(=O)CCC1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:33](=[O:35])[CH2:32][CH2:31][C:28]1[CH:27]=[CH:26][C:25]([NH:24][C:21]2[N:22]=[CH:23][C:18]([C:15]3[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=3)=[CH:19][N:20]=2)=[CH:30][CH:29]=1)[CH3:2]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 25517Ammonium ChlorideHCID 576326193-{4-[5-(4-Methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionic acid

Product 1

HCID 57632944HCID 57632944, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-(3-Diethylamino-propyl)-phenyl]-[S-(4-methoxy-phenyl)-pyrimidin-2-yl]-amine can be prepared by the following procedure. Diethylamine (10 mmol), EDC (25 mmol) and DMAP (0.1 mmol) are dissolved in dichloromethane (3 mL) and added to the crude 3-{4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionic acid dissolved in NMP (from example 5ao) at rt. After 3 h, sat. aq NH4Cl is added and the mixture is extracted with EtOAc. The combined extracts are dried over anhydrous Na2SO4 and solvent is removed. Purification by preparative HPLC yields N,N-diethyl-3-{4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-propionamide.

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe combined extracts are dried over anhydrous Na2SO4 and solvent
  3. customis removed
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-37a38a9d4e4245fe8820bd23a3047cb8
Source dataset
uspto-grants-2009_12
Patent number
US07638523B2

Reaction notes

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