Tetrabutylammonium Fluoride → HCID 49764704, compound

HRID 1893277Notes

Reaction equation

HRID 1893277 reaction equation
[OH:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][Si](C)(C)C)[CH:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[NH:21]1[CH2:24][CH:23]([NH:25][C:26]([CH2:28][NH:29][C:30](=[O:41])[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)=[O:27])[CH2:22]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[C:15]([C:11]1[CH:10]=[C:9]([C:2]2([OH:1])[CH2:7][CH2:6][CH:5]([N:21]3[CH2:24][CH:23]([NH:25][C:26]([CH2:28][NH:29][C:30](=[O:41])[C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:38])[F:39])[CH:32]=4)=[O:27])[CH2:22]3)[CH2:4][CH2:3]2)[CH:14]=[CH:13][CH:12]=1)#[CH:16]

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 59361594N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamideHCID 59541958HCID 59541958, compound

Product 1

HCID 49764704HCID 49764704, compound

Procedure

The title compound was prepared as a white solid by reductive amination of 4-hydroxy-4-(3-trimethylsilanylethynyl-phenyl)-cyclohexanone (as prepared in the previous step) and N-(azetidin-3-ylcarbamoylmethyl)-3-trifluoromethyl-benzamide (as prepared in step B of Example 4) using the procedure described in Step C of Example 4 followed by a TBAF work-up using the procedure described in Step D of Example 40.

Sources & evidence

ORD record
ord-8be0c24b1cd34d9b8ce4d7e897e91ab1
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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