Hydrochloric Acid → 4-(Benzyloxy)-1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

HRID 2387479Notes

Reaction equation

HRID 2387479 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].C(OCC)C>C(Cl)Cl>[ClH:33].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 250576454-(Benzyloxy)-1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)pyridin-2(1H)-one

Product 1

HCID 684552034-(Benzyloxy)-1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochlorideYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(benzyloxy)-1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (37.0 mg, 0.086 mmol) in CH2Cl2 (0.7 mL) was treated with anhydrous HCl in diethyl ether (86 μL, 0.086 mmol, 1.0 M). After stirring at ambient temperature for 4.5 h, the solids were collected by filtration, dissolved in CH3CN and H2O, partially concentrated, then lyophilized to yield the title compound (25.6 mg, 64%) as a light yellow solid: 1H NMR (500 MHz, DMSO-d6) δ 10.50 (br s, 1H), 8.23 (s, 1H), 7.85 (d, J=8.5 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.48-7.41 (m, 5H), 7.39-7.36 (m, 1H), 6.12 (dd, J=7.5, 3.0 Hz, 1H), 5.99 (d, J=3.0 Hz, 1H), 5.15 (s, 2H), 4.92 (br s, 2H), 3.99 (d, J=12.0 Hz, 2H), 3.70-3.68 (m, 4H), 3.53 (d, J=12.0 Hz, 2H), 3.19 (br m, 2H); ESI MS m/z 431 [M+H]+; HPLC (Method A) 99.3% (AUC), tR=13.9 min.

Workup

  1. filtrationthe solids were collected by filtration
  2. dissolutiondissolved in CH3CN
  3. concentrationH2O, partially concentrated

Sources & evidence

ORD record
ord-0a7a14f6a6104bcbaadfa0e82f88a3bd
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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