Trifluoroacetic acid → HCID 44253045, compound

HRID 1645248Notes

Reaction equation

HRID 1645248 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=1[S:44]([N:47]([CH2:51][CH2:52][O:53][CH2:54]C(O)=O)[CH:48]1[CH2:50][CH2:49]1)(=[O:46])=[O:45].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCCl>[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=1[S:44]([N:47]([CH2:51][CH2:52][O:53][CH2:54][C:14]([N:11]1[CH2:10][CH2:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)([CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:13][CH2:12]1)=[O:15])[CH:48]1[CH2:50][CH2:49]1)(=[O:46])=[O:45]

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57916235HCID 57916235, compoundHCID 57917551HCID 57917551, compound

Product 1

HCID 44253045HCID 44253045, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tert-butyl 4-(3-chlorophenyl)-4-(3-(pyrrolidin-1-yl)propyl)piperidine-1-carboxylate (0.15 g, 0.37 mmol) in dichloromethane (3 ml) was Boc-deprotected using standard reaction conditions (see step (vi)/example 25; TFA (3-13 eq.)) and added dropwise to a solution containing 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetic acid [carboxylic acid 2] (1 eq.), EDCI (1.5 eq.), HOBt (1 eq.) and DIPEA (6 eq.) in dichloromethane (5 ml) at 0° C. The resulting mixture was then stirred at room temperature for 16 h. The reaction mixture was diluted with dichloromethane and washed with aq. ammonium chloride, aq. sodium hydrogen carbonate and water respectively. The organic layer was dried over sodium sulfate, concentrated in vacuo and the crude product purified by chromatography (silica). Yield: 25%

Workup

  1. customBoc-deprotected using standard reaction conditions (
  2. additionadded dropwise to a solution
  3. washwashed with aq. ammonium chloride, aq. sodium hydrogen carbonate and water respectively
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe crude product purified by chromatography (silica)

Sources & evidence

ORD record
ord-2c242f5b887540b797d7212d89acc5fb
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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