Tetrabutylammonium Fluoride → HCID 25175473, compound

HRID 2190341Notes

Reaction equation

HRID 2190341 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH2:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:18]([NH:20][C:21]2[S:22][C:23]([Cl:37])=[C:24]([C:26]3[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:35])=[O:34])=[CH:28][CH:27]=3)[N:25]=2)=[O:19])=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:37][C:23]1[S:22][C:21]([NH:20][C:18](=[O:19])[N:17]([CH2:38][CH2:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:14]2[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][OH:8])=[CH:16][CH:15]=2)=[N:25][C:24]=1[C:26]1[CH:31]=[CH:30][C:29]([NH:32][S:33]([CH3:36])(=[O:34])=[O:35])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57586417HCID 57586417, compound

Product 1

HCID 25175473HCID 25175473, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenyl)-3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)urea (0.289 g, 0.373 mmol) in THF (2 mL) at room temperature was added TBAF (1 M in THF, 1.5 mL, 1.5 mmol). The reaction mixture was stirred at room temperature for 3 h and concentrated. Purification by flash column chromatography on silica gel (eluted with 3% to 10% MeOH in DCM) gave N-(4-(5-chloro-2-(((3,3-diphenylpropyl)(4-(2-hydroxyethyl)phenyl)carbamoyl)amino)-1,3-thiazol-4-yl)phenyl)methanesulfonamide 68. Mass spectrum, calculated for C34H33ClN4O4S2 660.2; found 661.2 (M++1).

Workup

  1. concentrationconcentrated
  2. customPurification by flash column chromatography on silica gel (eluted with 3% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-5c9e8db2876b47129ff7a935ca09d7f9
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

Loading…