Trifluoroacetic acid water → HCID 67494455, compound

HRID 2047042Notes

Reaction equation

HRID 2047042 reaction equation
[Br:1][C:2]1[C:3]([O:38][C:39]2[CH:44]=[CH:43][C:42]([S:45]([CH3:48])(=[O:47])=[O:46])=[CH:41][CH:40]=2)=[N:4][C:5]2[N:6]([N:25]=[CH:26][C:27]=2[C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:7]=1[N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C.C(O)(C(F)(F)F)=O.O>>[Br:1][C:2]1[C:3]([O:38][C:39]2[CH:40]=[CH:41][C:42]([S:45]([CH3:48])(=[O:47])=[O:46])=[CH:43][CH:44]=2)=[N:4][C:5]2[N:6]([N:25]=[CH:26][C:27]=2[C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:7]=1[NH2:8]

Participants

3

Reactant 2

HCID 22392675Trifluoroacetic acid waterHCID 67494315HCID 67494315, compound

Product 1

HCID 67494455HCID 67494455, compound

Procedure

The crude, 6-bromo-5-(4-(methylsulfonyl)phenoxy)-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine from above step E was treated with 50% TFA/H2O (3 mL) and stirred at room temperature for 1 h. Solvent was removed to yield thick oil which was purified by prep HPLC to give the final product. 6-bromo-5-(4-(methylsulfonyl)phenoxy)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-7-amine. HPLC-MS tR=1.37 min (UV254 nm); mass calculated for formula C22H16BrN5O3S2 509.0, observed LCMS m/z 510.0 (M+H).

Workup

  1. customSolvent was removed
  2. customto yield thick oil which
  3. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-d2b7c7340099486fa03a94a10a60bc79
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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