Hydrochloric Acid → HCID 73335726, compound

HRID 710639Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:31])[CH:18]([N:21]4[C:25]([CH3:26])=[CH:24][C:23]([C:27](O)([CH3:29])[CH3:28])=[N:22]4)[CH2:19][CH3:20])[C:11]=3[CH:10]=[N:9]2)=[CH:4][CH:3]=1.Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][CH2:13][N:12]([C:17](=[O:31])[CH:18]([N:21]4[C:25]([CH3:26])=[CH:24][C:23]([C:27]([CH3:29])=[CH2:28])=[N:22]4)[CH2:19][CH3:20])[C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 73335638HCID 73335638, compound

Product 1

HCID 73335726HCID 73335726, compound

Procedure

A portion of 1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-[3-(1-hydroxy-1-methyl-ethyl)-5-methyl-pyrazol-1-yl]butan-1-one was treated with 6 M HCl until complete. The reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide 12 mg of the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 8.47 (s, 1H), 7.44 (m, 2H), 7.14 (t, J=8.6 Hz, 2H), 6.14 (s, 1H), 5.42 (br s, 1H), 5.22 (dd, J=7.1, 8.2 Hz, 1H), 5.02 (br s, 1H), 3.80 (ddd, J=3.1, 7.8, 10.1 Hz, 1H), 3.47 (ddd, J=2.8, 9.0, 12.1 Hz, 1H), 2.74 (m, 2H), 2.33 (m, 1H), 2.23 (s, 3H), 2.15 (m, 1H), 2.10 (s, 3H) 1.87 (m, 1H), 1.78 (m, 1H), 0.98 (t, J=7.4 Hz, 3H); MS: (ES) m/z calculated for C23H27FN5O [M+H]+ 408.2, found 408.2.

Workup

customThe reaction slurry was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent)

Sources & evidence

ORD record: ord-566f7416f9024b51aef60435c0a3d4c1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181241B2

Reaction notes

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