3-(Trifluoromethyl)aniline → HCID 50913375, compound

HRID 1949084Notes

Reaction equation

HRID 1949084 reaction equation
C(OC([NH:8][C:9]1([C:25](O)=[O:26])[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])(=[O:17])=[O:16])[CH2:11][CH2:10]1)=O)(C)(C)C.[F:28][C:29]([F:38])([F:37])[C:30]1[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=1)[NH2:33]>>[F:28][C:29]([F:37])([F:38])[C:30]1[CH:31]=[C:32]([NH:33][C:25]([C:9]2([NH2:8])[CH2:14][CH2:13][N:12]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])(=[O:16])=[O:17])[CH2:11][CH2:10]2)=[O:26])[CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 58129355HCID 58129355, compound

Product 1

HCID 50913375HCID 50913375, compound

Procedure

In analogy to the procedure of the synthesis of [4-(4-tert-Butyl-phenylcarbamoyl)-1-(toluene-4-sulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (example 77, step 2) the title compound was prepared from 4-tert-Butoxycarbonylamino-1-(2-chloro-benzenesulfonyl)-piperidine-4-carboxylic acid through amide coupling with 3-trifluoromethyl-aniline (commercially available) followed by the removal of the protecting group with HCl in dioxane to afford the title compound after purification with preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. MS (m/e): 462.1 [(M+H)+].

Workup

  1. customfollowed by the removal of the protecting group with HCl in dioxane

Sources & evidence

ORD record
ord-6073a323d2184d649521473b4e95d4b7
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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