Trifluoroacetic acid → HCID 178480321, compound

HRID 874077Notes

Reaction equation

HRID 874077 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]1[CH:8]=[C:9]([O: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][O: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 178480322HCID 178480322, compound

Product 1

HCID 178480321HCID 178480321, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (trans-4-{[2-({5-[(2S)-1-methylpyrrolidin-2-yl]pyridin-3-yl}oxy)ethyl]carbamoyl}cyclohexyl)carbamate (preparation 35) (35 mg, 0.078 mmol) in DCM (3 mL) was treated with trifluoroacetic acid (1 mL). The resulting solution was stirred at ambient temperature overnight, 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 an orange gum (17 mg, 62%).

Workup

  1. concentrationafter which time it was 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-43326573e13a48cd88f4535dc1f37517
Source dataset
uspto-grants-2015_03
Patent number
US08980276B2

Reaction notes

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