Ethoxalyl chloride → (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-3,6-dihydro-2h-pyridin-1-yl)-oxo-acetic acid ethyl ester

HRID 76042Notes

Reaction equation

HRID 76042 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=4)=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1.CCN(C(C)C)C(C)C.Cl[C:38](=[O:44])[C:39]([O:41][CH2:42][CH3:43])=[O:40]>C(Cl)Cl>[CH2:42]([O:41][C:39](=[O:40])[C:38]([N:25]1[CH2:24][CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[O:12][C:11]([NH:10][C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([Cl:3])[CH:5]=4)=[N:15][CH:14]=3)=[CH:17][CH:18]=2)[CH2:27][CH2:26]1)=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 20884Ethoxalyl chlorideHCID 81531DiisopropylethylamineHCID 131731872(3-chlorophenyl)-{5-[4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-oxazol-2-yl}-amine bis HCl salt

Product 1

HCID 66615808(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-3,6-dihydro-2h-pyridin-1-yl)-oxo-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-chlorophenyl)-{5-[4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-oxazol-2-yl}-amine bis HCl salt (50 mg, 0.12 mmol) in DCM (1 mL) at 0° C. is added DIEA (0.052 mL, 0.3 mmol) and after stirring for 5 min, ethyl chlorooxoacetate (0.016 mL, 0.14 mmol) is added dropwise. The mixture is stirred for 2 h and the mixture is purified by RP-HPLC to give the title compound: 1H NMR (400 MHz, DMSO-D6) δ 1.30 (q, J=7.07 Hz, 3H) 2.58 (m, 2H) 3.55-3.90 (m, 2H) 4.07-4.20 (m, 1H) 4.32 (m, 2H) 6.21-6.29 (m, 1H) 7.00 (dd, J=7.45, 1.64 Hz, 1H) 7.34 (t, J=8.08 Hz, 1H) 7.47-7.60 (m, 6H) 7.86 (t, J=2.02 Hz, 1H); (M+H)+452.1.

Workup

  1. stirringThe mixture is stirred for 2 h
  2. customthe mixture is purified by RP-HPLC

Sources & evidence

ORD record
ord-61ce77b122f9463dbb8441c391f5e820
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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