Trifluoroacetic acid → HCID 68427754, compound

HRID 502262Notes

Reaction equation

HRID 502262 reaction equation
[CH:1]([O:4][C:5](=[O:38])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH:34]3[CH2:37][CH2:36][CH2:35]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH2:26][CH:27]2[CH2:31][O:30]C(C)(C)[O:28]2)[CH:16]=3)=[CH:9][CH:8]=1)([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([O:4][C:5](=[O:38])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([CH:34]3[CH2:35][CH2:36][CH2:37]3)[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH2:25][CH2:26][CH:27]([OH:28])[CH2:31][OH:30])[CH:16]=3)=[CH:11][CH:12]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68427202HCID 68427202, compound

Product 1

HCID 68427754HCID 68427754, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-{3-cyano-1-cyclobutyl-6-[2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-1H-indol-2-yl}-phenyl)-carbamic acid isopropyl ester (70 mg, 0.135 mmole) in DCM (2 mL) is added TFA (10 uL). The resulting mixture is stirred at ambient temperature for 2 h. The solvent is removed under reduced pressure and the residue is diluted with ethyl acetate and triturated with hexane and the precipitate collected by filtration and washed well with 50% ethyl acetate in hexane and dried in vacuo to afford {4-[3-cyano-1-cyclobutyl-6-(3,4-dihydroxy-butoxy)-1H-indol-2-yl]-phenyl}-carbamic acid isopropyl ester, compound 1429, 45 mg, (70%).

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionthe residue is diluted with ethyl acetate
  3. customtriturated with hexane
  4. filtrationthe precipitate collected by filtration
  5. washwashed well with 50% ethyl acetate in hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-ebcf0cba35b145b7bb67bcdc5d890c5b
Source dataset
uspto-grants-2010_08
Patent number
US07772271B2

Reaction notes

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