Trifluoroacetic acid → HCID 18445855, compound

HRID 460677Notes

Reaction equation

HRID 460677 reaction equation
C([O:5][C:6](=[O:46])[CH:7]([NH:14][C:15]([C:17]1[CH:45]=[C:20]2[N:21]=[C:22]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)[CH:23]=[C:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:27][CH:26]=3)[N:19]2[N:18]=1)=[O:16])[CH2:8][O:9]C(C)(C)C)(C)(C)C.FC(F)(F)C(O)=O>O>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([C:22]2[CH:23]=[C:24]([C:25]3[CH:26]=[CH:27][C:28]([O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:29][CH:30]=3)[N:19]3[N:18]=[C:17]([C:15]([NH:14][CH:7]([CH2:8][OH:9])[C:6]([OH:46])=[O:5])=[O:16])[CH:45]=[C:20]3[N:21]=2)=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69707195HCID 69707195, compound

Product 1

HCID 18445855HCID 18445855, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 3-tert-butoxy-2-{[5-(4-chloro-phenyl)-7-(4-phenoxy-phenyl)-pyrazolo[1,5-α]pyrimidine-2-carbonyl]-amino}-propionic acid tert-butyl ester was treated with 1 mL of 95:5 trifluoroacetic acid (TFA):H2O, and the resulting solution was stirred at rt for 1.5 h, after which time it was quenched by the addition of 2 mL of 1:1 acetonitrile:water. The mixture was then concentrated and lyophilized to afford 11.2 mg (93% yield over 2 steps) of desired 2-{[5-(4-chloro-phenyl)-7-(4-phenoxy-phenyl)-pyrazolo[1,5-α]pyrimidine-2-carbonyl]-amino}-3-hydroxy-propionic acid, as a solid whose 1H NMR spectrum was consistent with its structure. For entry 260: LC-MS calcd. for C28H21ClN4O5 [M+H]+: 529.12; found: 529.1.

Workup

  1. customafter which time it was quenched by the addition of 2 mL of 1:1 acetonitrile
  2. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-71fa546c64ad48b0a83b6c4379369d77
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Reaction notes

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