Trifluoroacetic acid → HCID 131732819, compound

HRID 571389Notes

Reaction equation

HRID 571389 reaction equation
COC1C=CC(C[NH:8][C:9]([NH:11][C:12]2[N:17]=[CH:16][C:15]3[C:18]([C:40]4[CH:45]=[CH:44][N:43]=[C:42]([CH3:46])[CH:41]=4)=[N:19][N:20](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:14]=3[CH:13]=2)=[O:10])=CC=1.[C:49]([OH:55])([C:51]([F:54])([F:53])[F:52])=[O:50]>O1CCOCC1>[OH:55][C:49]([C:51]([F:54])([F:53])[F:52])=[O:50].[CH3:46][C:42]1[CH:41]=[C:40]([C:18]2[C:15]3[CH:16]=[N:17][C:12]([NH:11][C:9]([NH2:8])=[O:10])=[CH:13][C:14]=3[NH:20][N:19]=2)[CH:45]=[CH:44][N:43]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 117601502HCID 117601502, compound

Product 1

HCID 131732819HCID 131732819, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A crude mixture of 1-(4-methoxybenzyl)-3-(3-(2-methylpyridin-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)urea prepared according to Scheme 6 (35 mg, 0.055 mmol) in 1,4-dioxane (0.25 mL) was treated at room temperature with TFA (0.25 mL) and the reaction mixture stirred for 5 h, then additional TFA (0.25 mL) was added and the reaction mixture stirred for 16 h at room temperature and then concentrated in vacuo. The residue was purified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase, eluting with a H2O/MeCN gradient with 0.1% TFA), to give 1-(3-(2-methylpyridin-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)urea TFA salt as a yellow solid (4 mg, 0.01 mmol, 19%). MS ESI calc'd. for C13H13N6O [M+H]+ 269, found 269. 1H NMR (600 MHz, DMSO-d6) δ 13.82 (br s, 1H), 9.31 (s, 1H), 9.19 (s, 1H), 8.70 (s, 1H), 8.30-8.15 (m, 2H), 7.88 (s, 1H), 2.70 (s, 3H).

Workup

  1. customprepared
  2. stirringthe reaction mixture stirred for 16 h at room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by MS-directed reverse phase preparative-HPLC (C-18 stationary phase
  5. washeluting with a H2O/MeCN gradient with 0.1% TFA),

Sources & evidence

ORD record
ord-6c0d483f6b05498bbc14a83fdb94b8ee
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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