Hydrochloric Acid → HCID 86707068, compound

HRID 57872Notes

Reaction equation

HRID 57872 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([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:5]=[N:4]1)[CH3:2].Cl>CO.O1CCOCC1>[N:23]1([C:21]2[N:22]=[C:17]([N:16]3[C:10]4[CH:9]=[C:8]([C:6]5[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=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 2

HCID 313Hydrochloric AcidHCID 86707067Tert-butyl 4-[6-[6-(1-ethylpyrazol-4-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate

Product 1

HCID 86707068HCID 86707068, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-[6-[6-(1-ethylpyrazol-4-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate (0.2596 mmol; 127.1 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 163 as an off-white solid (34.9 mg, 34%). 1H NMR (400 MHz, DMSO) δ 9.17-9.12 (s, 1H), 8.60-8.56 (s, 1H), 8.55-8.52 (s, 1H), 8.39-8.36 (s, 1H), 8.27-8.24 (s, 1H), 8.12-8.08 (s, 1H), 7.91-7.85 (s, 1H), 4.25-4.17 (q, J=7.3 Hz, 2H), 3.92-3.80 (dt, J=10.3, 5.5 Hz, 4H), 3.05-2.95 (m, 2H), 2.79-2.71 (m, 2H), 1.95-1.82 (m, 2H), 1.46-1.40 (t, J=7.3 Hz, 3H); MS (ESI) m/z: 390.2 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-35ddedbbef864000b726e223854b1839
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

Loading…