Trifluoroacetic acid → HCID 44252308, compound

HRID 1645251Notes

Reaction equation

HRID 1645251 reaction equation
[F: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]([CH:48]1[CH2:50][CH2:49]1)[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]([F: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])(=[O:46])=[O:45]

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57916235HCID 57916235, compoundHCID 57917513HCID 57917513, compound

Product 1

HCID 44252308HCID 44252308, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tert-butyl 4-(3-fluorophenyl)-4-(3-(pyrrolidin-1-yl)propyl)piperidine-1-carboxylate (0.2379 mmol, 1.0 eq.) 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 (1.0 eq.) and DIPEA (6.0 eq.) in dichloromethane (5 ml) at 0° C. The mixture was then stirred at room temperature for 16 hrs. The reaction mixture was diluted with dichloromethane and extracted 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 column chromatography (silica). Yield: 30%

Workup

  1. customBoc-deprotected using standard reaction conditions (
  2. additionadded dropwise to a solution
  3. extractionextracted 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 column chromatography (silica)

Sources & evidence

ORD record
ord-7c8de36a435d46b1ae7e146e235bac40
Source dataset
uspto-grants-2012_02
Patent number
US08124624B2

Reaction notes

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