Hydrochloric Acid → HCID 53378070, compound

HRID 389500Notes

Reaction equation

HRID 389500 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:22]=[N:23][N:24]([CH:26]3[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]3)[CH:25]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[CH:20]=[CH:19][CH:18]=[C:17]4[C:12]=3[CH:13]=[CH:14][N:15]=[CH:16]4)[O:8][C:7]=12.Cl>C(Cl)Cl>[NH:28]1[CH2:27][CH:26]([N:24]2[CH:25]=[C:21]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[C:7]4[O:8][C:9]([C:11]5[CH:20]=[CH:19][CH:18]=[C:17]6[C:12]=5[CH:13]=[CH:14][N:15]=[CH:16]6)=[CH:10][C:6]=34)[CH:22]=[N:23]2)[CH2:29]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66759995HCID 66759995, compound

Product 1

HCID 53378070HCID 53378070, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-{4-[7-amino-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-4-yl]-1H-pyrazol-1-yl}azetidine-1-carboxylate in DCM (10 mL) was treated with HCl (4 M in 1,4-dioxane, 2.57 mL, 10.3 mmol) and stirred at RT for 16 h. The reaction was then concentrated in vacuo to a solid which was purified by MDP to afford 1.3 mg (1%) of the title compound. 1H NMR (400 MHz, CD3OD) δ 9.77 (br. s, 1H), 8.93 (d, J=6.32 Hz, 1H), 8.70 (d, J=7.33 Hz, 2H), 8.59 (d, J=8.34 Hz, 1H), 8.41 (s, 1H), 8.21 (s, 1H), 8.11 (t, J=7.96 Hz, 1H), 7.91 (d, J=4.29 Hz, 2H), 5.58 (s, 1H), 4.63 (dd, 4H); MS (ESI): 383.15 [M+H]+; HPLC tR=0.72 min (TOF: polar—3 min).

Workup

  1. concentrationThe reaction was then concentrated in vacuo to a solid which
  2. customwas purified by MDP

Sources & evidence

ORD record
ord-485a703e712340faaa604bff3d79a88e
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…