Trifluoroacetic acid → HCID 86714603, compound

HRID 624756Notes

Reaction equation

HRID 624756 reaction equation
[CH:1]1([N:4]([C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:21]=[O:22])=[C:16]3[N:15]=[C:14]([C:23]3[CH:27]=[C:26]([CH2:28][OH:29])[S:25][CH:24]=3)[CH:13]=2)C(=O)OC(C)(C)C)[CH2:3][CH2:2]1.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>ClCCl>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[CH:1]1([NH:4][C:12]2[N:17]3[N:18]=[CH:19][C:20]([CH:21]=[O:22])=[C:16]3[N:15]=[C:14]([C:23]3[CH:27]=[C:26]([CH2:28][OH:29])[S:25][CH:24]=3)[CH:13]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714604HCID 86714604, compound

Product 1

HCID 86714603HCID 86714603, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl cyclopropyl(3-formyl-5-(5-(hydroxymethyl)thiophen-3-yl)pyrazolo[1,5-a]pyrimidine-7-yl)carbamate (20 mg, 0.05 mmol) was dissolved in dichloromethane (0.5 mL) and trifluoroacetic acid (0.5 mL). After 1 h, the solution was concentrated under a stream of air. The residue was purified via preparative HPLC to furnish 7-(cyclopropylamino)-5-(5-(hydroxymethyl)thiophen-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 2,2,2-trifluoroacetate (4.8 mg, 23%).

Workup

  1. concentrationthe solution was concentrated under a stream of air
  2. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-012729648ba3484a9de8a8bcb04ac1cc
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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