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

HRID 422074Notes

Reaction equation

HRID 422074 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[N:22]([CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[N:21]=[CH:20]5)[C:11](=[O:33])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.Cl.C(OCC)C>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:17]4[CH:18]=[C:19]5[C:23](=[CH:24][CH:25]=4)[N:22]([CH2:26][CH2:27][N:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[N:21]=[CH:20]5)[C:11](=[O:33])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 250170332-(4-Chlorophenyl)-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one

Product 1

HCID 666728672-(4-Chlorophenyl)-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one HydrochlorideYield 187.4%

Procedure

A solution of 2-(4-chlorophenyl)-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one (6.7 mg, 0.014 mmol) in CDCl3 (0.7 mL) was treated with anhydrous HCl in diethyl ether (14.5 μL, 0.014 mmol, 1.0 M). After stirring at ambient temperature for one hour, the reaction mixture was concentrated, dissolved in CH3CN and H2O, partially concentrated, then lyophilized to yield the title compound (6.5 mg, 91%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 9.81 (br s, 0.5H), 8.28 (s, 1H), 7.92-7.89 (m, 4H), 7.68 (d, J=7.5 Hz, 1H), 7.63 (s, 1H), 7.56 (d, J=8.5 Hz, 2H), 7.53 (dd, J=9.0, 1.5 Hz, 1H), 6.91 (d, J=7.5 Hz, 1H), 4.86 (t, J=6.0 Hz, 2H), 3.76 (t, J=6.0 Hz, 2H), 3.57-3.56 (m, 2H), 3.11-3.07 (m, 2H), 2.01 (br m, 2H), 1.87-1.84 (br m, 2H); ESI MS m/z 459 [M+H]+; HPLC (Method A) 97.0% (AUC), tR=17.0 min.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutiondissolved in CH3CN
  3. concentrationH2O, partially concentrated

Sources & evidence

ORD record
ord-fe15367eb8474ebdb52264c9f4645508
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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