Hydrochloric Acid → HCID 66760532, compound

HRID 389503Notes

Reaction equation

HRID 389503 reaction equation
[CH:1]1[C:10]2[C:5](=[C:6]([C:11]3[O:34][C:14]4=[C:15]([NH2:33])[N:16]=[CH:17][C:18]([C:19]5[CH:20]=[N:21][N:22]([CH2:24][CH2:25][O:26]C6CCCCO6)[CH:23]=5)=[C:13]4[CH:12]=3)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.Cl>CO>[NH2:33][C:15]1[N:16]=[CH:17][C:18]([C:19]2[CH:20]=[N:21][N:22]([CH2:24][CH2:25][OH:26])[CH:23]=2)=[C:13]2[CH:12]=[C:11]([C:6]3[CH:7]=[CH:8][CH:9]=[C:10]4[C:5]=3[CH:4]=[CH:3][N:2]=[CH:1]4)[O:34][C:14]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53378069HCID 53378069, compound

Product 1

HCID 66760532HCID 66760532, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(isoquinolin-5-yl)-4-{1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-pyrazol-4-yl}furo[2,3-c]pyridin-7-amine (20.0 mg, 0.0439 mmol) was dissolved in MeOH (0.5 mL) and HCl (4 M in 1,4-dioxane, 0.50 mL, 2.0 mmol) was added. The reaction stirred at RT for 16 h. The reaction was concentrated in vacuo to a solid. Purification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc) afforded 1.6 mg (10%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 9.36 (s, 1H), 8.60 (d, J=6.06 Hz, 1H), 8.52 (d, J=6.32 Hz, 1H), 8.38 (dd, J=7.33, 1.26 Hz, 1H), 8.27 (d, J=8.34 Hz, 1H), 8.14 (s, 1H), 7.96 (d, J=1.01 Hz, 2H), 7.82-7.89 (m, 1H), 7.55 (s, 1H), 4.32-4.38 (m, 2H), 3.97 (t, 2H); MS (ESI): 372.14 [M+H]+; HPLC tR=0.82 min (TOF: polar—3 min).

Workup

  1. concentrationThe reaction was concentrated in vacuo to a solid
  2. customPurification by flash chromatography (0 to 10% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-1656fc68535a45cba94cef5bba9e3603
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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