Hydrochloric Acid → HCID 178430684, compound

HRID 57874Notes

Reaction equation

HRID 57874 reaction equation
F[C:2]1[C:7]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][N:16]([C:17]4[N:22]=[C:21]([N:23]5[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)[CH:20]=[N:19][CH:18]=4)[C:10]=3[CH:9]=2)=[CH:6][C:5]([CH3:37])=[CH:4][N:3]=1.Cl.C[OH:40]>O1CCOCC1>[N:23]1([C:21]2[N:22]=[C:17]([N:16]3[C:10]4[CH:9]=[C:8]([C:7]5[C:2]([OH:40])=[N:3][CH:4]=[C:5]([CH3:37])[CH:6]=5)[N:13]=[CH:12][C:11]=4[CH:14]=[N:15]3)[CH:18]=[N:19][CH:20]=2)[CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86707069Tert-butyl 4-[6-[6-(2-fluoro-5-methyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate

Product 1

HCID 178430684HCID 178430684, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-[6-[6-(2-fluoro-5-methyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate (0.2113 mmol; 106.6 mg) in Methanol (5 mL) was added hydrochloric acid, 4.0 M in 1,4-Dioxane (5 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 164 as a by-product (18.7 mg, 22%). 1H NMR (400 MHz, DMSO) δ 9.89-9.85 (s, 1H), 9.25-9.20 (s, 1H), 8.64-8.60 (s, 1H), 8.56-8.52 (d, J=2.6 Hz, 1H), 8.41-8.38 (s, 1H), 8.08-8.05 (s, 1H), 7.33-7.30 (s, 1H), 3.95-3.84 (m, 4H), 2.99-2.93 (m, 2H), 2.71-2.66 (m, 2H), 2.15-2.13 (s, 3H), 1.88-1.81 (m, 2H); MS (ESI) m/z: 403.2 [M+H]+

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-5f62aed64aa14555912d68cb5a48417e
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

Loading…