Ammonium Chloride → HCID 67461146, compound

HRID 553838Notes

Reaction equation

HRID 553838 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[I-].[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:46])[C@@H:20]([NH:30][C:31]([C:33]2[CH:38]=[C:37](Cl)[N:36]=[C:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:34]=2)=[O:32])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:15][CH2:14]1)=[O:12])[CH3:9].[NH4+].[Cl-]>CN(C=O)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCN(CC)CC>[CH2:8]([O:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:46])[C@@H:20]([NH:30][C:31]([C:33]2[CH:38]=[C:37]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[N:36]=[C:35]([C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:34]=2)=[O:32])[CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:15][CH2:14]1)=[O:12])[CH3:9]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 30165Iodide IonHCID 66111TrimethylsilylacetyleneHCID 866224044-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 67461146HCID 67461146, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

NEt3 (0.249 ml) and trimethylsilylacetylene (0.254 ml) in DMF (4.5 ml) were syringed into a flask containing cupper iodide (8.9 mg), bis-(triphenylphosphine) palladium(II)-dichloride (22.5 mg) and 4-{(S)-4-tert-butoxycarbonyl-2-[(6-chloro-2-phenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (500 mg) under argon. The mixture was allowed to stir at RT overnight. A saturated NH4Cl solution was added and the resulting mixture was extracted with EA. The org. phases were dried (Na2SO4) and evaporated off. Column chromatography (EA/Hept 1/2 to 1/1.5) afforded 339 mg of the desired compound.

Workup

  1. extractionthe resulting mixture was extracted with EA
  2. dry with materialphases were dried (Na2SO4)
  3. customevaporated off

Sources & evidence

ORD record
ord-fda0809aef4a4e639e97f6c4e9b37f2b
Source dataset
uspto-grants-2011_11
Patent number
US08048881B2

Reaction notes

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