Hydrochloric Acid → HCID 66672727, compound

HRID 422089Notes

Reaction equation

HRID 422089 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1.Cl.C(OCC)C>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([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:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25017297HCID 25017297, compound

Product 1

HCID 66672727HCID 66672727, compoundYield 171.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-chlorophenyl)-5-(1-(2-(pyrrolidine-1-yl)ethyl)-1H-indazol-5-yl)furo[3,2-c]pyridine-4(5H)-one (83.mg, 0.18 mmol) in CH2Cl2 (1.5 mL) was treated with anhydrous HCl in diethyl ether (0.18 μL, 0.18 mmol, 1.0 M). After stirring at ambient temperature for 3 h, the solids were collected by filtration and dried to yield the title compound (76.3 mg, 84%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 9.97 (br s, 1H), 8.24 (s, 1H), 7.96 (t, J=2.0 Hz, 1H), 7.92-7.85 (m, 3H), 7.71 (s, 1H), 7.69 (d, J=7.5 Hz, 1H), 7.54-7.51 (m, 2H), 7.45 (dd, J=8.0, 1.5 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 4.87 (t, J=6.0 Hz, 2H), 3.75-3.74 (m, 2H), 3.55 (br m, 2H), 3.08 (br m, 2H), 2.01 (br m, 2H), 1.85-1.84 (br m, 2H); ESI MS m/z 459 [M+H]+; HPLC (Method A) >99% (AUC), tR=16.0 min.

Workup

  1. filtrationthe solids were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-6c8bf9ac2ee64d0c8992ff8af6ef97f5
Source dataset
uspto-grants-2012_01
Patent number
US08101632B2

Reaction notes

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