Tributylphosphine → HCID 23634389, compound

HRID 2384898Notes

Reaction equation

HRID 2384898 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:18][C:19]([C:21]2[S:22][C:23]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)=[CH:24][C:25]=2[CH2:26][CH2:27]O)=[O:20])[CH:6]=[CH:7][C:8]=1[NH:9][C:10](=[O:17])[CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(P(CCCC)CCCC)CCC.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.CCOCC>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:23]2[S:22][C:21]3[C:19](=[O:20])[N:18]([C:5]4[CH:6]=[CH:7][C:8]([NH:9][C:10](=[O:17])[CH2:11][N:12]5[CH2:16][CH2:15][CH2:14][CH2:13]5)=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:27][CH2:26][C:25]=3[CH:24]=2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86629207HCID 86629207, compound

Product 1

HCID 23634389HCID 23634389, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 5-(4-chloro-phenyl)-3-(2-hydroxy-ethyl)-thiophene-2-carboxylic acid [3-methoxy-4-(2-pyrrolidin-1-yl-acetylamino)-phenyl]-amide (623 μmol, 320 mg) and tri-n-butylphosphine (934 μmol, 233 μL) in tetrahydrofuran (5 mL) then add dropwise via syringe diisopropyl azodicarboxylate (934 μmol, 185 μL). Stir the mixture at room temperature for 4 h. Dilute the mixture with 15 mL of Et2O, filter the resulting solid, and dry under vacuum at 60° C. to afford 195 mg (63%) of N-{4-[2-(4-chloro-phenyl)-7-oxo-4,7-dihydro-5H-thieno[2,3-c]pyridin-6-yl]-2-methoxy-phenyl}-2-pyrrolidin-1-yl-acetamide. Prepare the hydrochloride salt of the free base using 1N HCl in ethanol. Dilute the salt solution in ether then filter off the product. Dry in vacuo to obtain the title compound. MS/ES m/z (35Cl) 496.2 [M+H]+.

Workup

  1. filtrationfilter the resulting solid
  2. customdry under vacuum at 60° C.

Sources & evidence

ORD record
ord-4c930377fec3478e9dca3ae8ffee2381
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

Loading…