Trifluoroacetic acid water → HCID 56848530, compound

HRID 334372Notes

Reaction equation

C[Si](C)(C)CCOC[N:7](COCC[Si](C)(C)C)[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:34][CH2:33][C:32]([CH2:36][OH:37])([OH:35])[CH2:31][CH2:30]2)[C:9]=1[Br:38].C(O)(C(F)(F)F)=O.O>>[NH2:7][C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)=[CH:21][CH:22]=3)=[C:12]2[N:11]=[C:10]([CH:29]2[CH2:34][CH2:33][C:32]([CH2:36][OH:37])([OH:35])[CH2:31][CH2:30]2)[C:9]=1[Br:38]

Participants

Reactant 2

HCID 22392675Trifluoroacetic acid water

HCID 66583827HCID 66583827, compound

Product 1

HCID 56848530HCID 56848530, compoundYield 39.3%

Procedure

4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol (385 mg, 0.510 mmol) was treated with a mixture of TFA/H2O (2/2 mL) at rt overnight. The reaction mixture was evaporated to dryness and purified by a reverse phase HPLC to afford 4-(7-amino-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol as a pale yellow solid (99 mg). HPLC-MS TR=3.27 min (isomer 1) and 3.32 min (isomer 2) (UV 254 nm, 10 min method); mass calculated for formula C24H24BrN5O2 493.1, observed LCMS m/z 494 (M+H).

Workup

customThe reaction mixture was evaporated to dryness
custompurified by a reverse phase HPLC

Sources & evidence

ORD record: ord-f6b110a16b8a47cb8c2d625d7f03256c
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883801B2

Reaction notes

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