Trifluoroacetic acid → HCID 178480319, compound

HRID 874075Notes

Reaction equation

HRID 874075 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][CH2:15][NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH2:20]2)=[O:18])[CH:10]=[N:11][CH:12]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:25][C@H:22]1[CH2:21][CH2:20][C@H:19]([C:17]([NH:16][CH2:15][CH2:14][CH2:13][C:9]2[CH:10]=[N:11][CH:12]=[C:7]([C@@H:3]3[CH2:4][CH2:5][CH2:6][N:2]3[CH3:1])[CH:8]=2)=[O:18])[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178480320HCID 178480320, compound

Product 1

HCID 178480319HCID 178480319, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl {trans-4-[(3-{5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}propyl)carbamoyl]cyclohexyl}carbamate (preparation 13) (130 mg, 0.29 mmol) in DCM (3 mL) was treated with trifluoroacetic acid (1 mL). The resulting solution was stirred at ambient temperature for 2 hours after which time it was concentrated in vacuo. The residue was dissolved in MeOH and applied to an SCX-2 cartridge and eluted with MeOH followed by ammonia in MeOH (2M). The fractions containing product were concentrated in vacuo to give the title compound as a colourless gum (98 mg, 97%).

Workup

  1. concentrationwas concentrated in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. washeluted with MeOH
  4. additionThe fractions containing product
  5. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-edde4b061cfc45139e4ea5e071c36f3f
Source dataset
uspto-grants-2015_03
Patent number
US08980276B2

Reaction notes

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