Hydrochloric Acid → HCID 11775533, compound

HRID 2181408Notes

Reaction equation

HRID 2181408 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:28]3[CH2:33][CH2:32][N:31](C(OCC)=O)[CH2:30][CH2:29]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[N:14]=2)=[CH:4][CH:3]=1.[Si](I)(C)(C)C.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.C(O)CC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[N:14]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 85247Trimethylsilyl iodideHCID 60003257HCID 60003257, compound

Product 1

HCID 11775533HCID 11775533, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6212ChloroformSolvent

Procedure

4-(4-Fluorophenyl)-2-(1-ethoxycarbonylpiperidin-4-yl)-5-(2-(1-(S)-phenylethyl)amino-4-pyrimidinyl)thiazole (2.4 g 4.5 mmol) was dissolved in CHCl3 (45 ml) and treated with Me3SiI (1.8 ml 13.5 mmol) at 60° C. for 6 h. The reaction mixture was combined with 6M HCl in propanol (18.5 ml), homogenized by vigorous stirring, poured on 2N NaOH and extracted twice with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, evaporated to dryness and purified by SiO2 chromatography (tert.butyl methyl ether/MeOH/NH3conc. 95/4.5/0.5 to 80/18/2) to yield the title compound (1.8 g 87%) as a white foam.

Workup

  1. extractionextracted twice with CH2Cl2
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified by SiO2 chromatography (tert.butyl methyl ether/MeOH/NH3conc. 95/4.5/0.5 to 80/18/2)

Sources & evidence

ORD record
ord-c09cbcc108824cb896a6a1a497224005
Source dataset
uspto-grants-2005_05
Patent number
US06891039B2

Reaction notes

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