Hydrochloric Acid → HCID 178461055, compound

HRID 1943883Notes

Reaction equation

HRID 1943883 reaction equation
Cl.CC1(C)[O:7][CH:6]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([C:16]3[C:24]4[C:19](=[N:20][CH:21]=[C:22]([NH:25][C:26](=[O:42])[C:27]5[C:32]([F:33])=[CH:31][CH:30]=[C:29]([NH:34][S:35]([CH2:38][CH2:39][CH3:40])(=[O:37])=[O:36])[C:28]=5[F:41])[CH:23]=4)[NH:18][N:17]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:5][O:4]1>C1COCC1.CO>[OH:7][CH:6]([CH2:5][OH:4])[CH2:8][O:9][C:10]1[CH:11]=[C:12]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[C:22]([NH:25][C:26](=[O:42])[C:27]4[C:32]([F:33])=[CH:31][CH:30]=[C:29]([NH:34][S:35]([CH2:38][CH2:39][CH3:40])(=[O:37])=[O:36])[C:28]=4[F:41])[CH:23]=3)[NH:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178461053HCID 178461053, compound

Product 1

HCID 178461055HCID 178461055, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1N HCl (1.0 mL) was added to a solution of N-(3-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.050 g, 0.083 mmol) in THF/MeOH (2:1, 3 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was taken up in ethyl acetate (50 mL) and saturated NaHCO3 (50 mL). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with ethyl acetate to give N-(3-(3-(2,3-dihydroxypropoxy)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-2,6-difluoro-3-(propylsulfonamido)benzamide (0.008 g, 17%) as a solid. 1H NMR (400 MHz, CD3OD) δ 9.0 (s, 1H), 8.7 (s, 1H), 7.7 (m, 1H), 7.6-7.4 (m, 3H), 7.1 (m, 1H), 7.0 (m, 1H), 4.2 (m, 1H), 4.1-4.0 (m, 3H), 3.7 (m, 1H), 3.1 (m, 2H), 1.9 (m, 2H), 1.1 (t, J=7.6 Hz, 3H); m/z (APCI-neg) M−1=560.1.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-432d2232a5034c6298e5ae1841f1adfe
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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