Hydrochloric Acid → 2-Phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one Hydrochloride

HRID 422072Notes

Reaction equation

HRID 422072 reaction equation
[C:1]1([C:7]2[O:15][C:14]3[CH:13]=[CH:12][N:11]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[N:20]=[CH:19]5)[C:10](=[O:32])[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:33]>C(Cl)Cl.CCOCC>[ClH:33].[C:1]1([C:7]2[O:15][C:14]3[CH:13]=[CH:12][N:11]([C:16]4[CH:17]=[C:18]5[C:22](=[CH:23][CH:24]=4)[N:21]([CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][CH2:30][CH2:31]4)[N:20]=[CH:19]5)[C:10](=[O:32])[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 248575972-Phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one

Product 1

HCID 666728012-Phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one HydrochlorideYield 48%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenyl-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one (27.6 mg, 0.065 mmol) in CH2Cl2 (0.5 mL) was treated with anhydrous HCl in diethyl ether (65.0 μL, 0.065 mmol, 1.0 M). After stirring at ambient temperature for one hour, the reaction mixture was diluted with Et2O (50 mL). The resulting solids were collected by filtration and dried in a vacuum oven to yield the title compound (14.6 mg, 48%) as a brown solid. 1H NMR (500 MHz, DMSO-d6) δ 10.07 (br s, 0.5H), 8.28 (s, 1H), 7.92-7.89 (m, 4H), 7.66 (d, J=7.5 Hz, 1H), 7.56-7.48 (m, 4H), 7.40 (t, J=7.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 4.87 (t, J=6.0 Hz, 2H), 3.77-3.73 (m, 2H), 3.56-3.55 (m, 2H), 3.09-3.06 (m, 2H), 2.01 (br m, 2H), 1.89-1.84 (br m, 2H); ESI MS m/z 425 [M+H]+; HPLC (Method A) 95.4% (AUC), tR=15.3 min.

Workup

  1. filtrationThe resulting solids were collected by filtration
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-ac334e695a1b406c953bbe3cd6ec10ad
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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