Trifluoroacetic acid → HCID 59320954, compound

HRID 341161Notes

Reaction equation

HRID 341161 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:28]=[N:29][N:30]3[CH:35]=[C:34]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)[CH:33]=[N:32][C:31]=23)[CH:22]=1)=[O:19])(C)(C)C>C(Cl)Cl>[NH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:28]=[N:29][N:30]3[CH:35]=[C:34]([C:36]4[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=4)[CH:33]=[N:32][C:31]=23)[CH:22]=1)=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59320984HCID 59320984, compound

Product 1

HCID 59320954HCID 59320954, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (2 ml) was added slowly to a stirred suspension of [2-(3-{3-[6-(4-Fluoro-phenyl)-pyrazolo[1,5-a]pyrimidin-3-yl]phenyl}ureido)-ethyl]carbamic acid tert-butyl ester (390 mg, 0.80 mmol) in CH2Cl2 (4 ml) at RT. After 1 hour the volatiles were removed in vacuo. The residue was taken up in MeOH and loaded on a SCX cartridge (20 g). Eluting with 2M NH3. MeOH and removal of the solvent in vacuo gave the title compound (155 mg) as a yellow solid.

Workup

  1. customAfter 1 hour the volatiles were removed in vacuo
  2. washEluting with 2M NH3
  3. customMeOH and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-8380a298699f4a52b87c4b8a31549258
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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