Hydrochloric Acid → 1-(1-(2-Morpholinoethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one hydrochloride

HRID 2390437Notes

Reaction equation

HRID 2390437 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([N:18]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=5)=[CH:20][C:19]4=[O:34])=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[CH2:3][CH2:2]1.[ClH:35]>C(Cl)Cl.CCOCC>[ClH:35].[O:1]1[CH2:2][CH2:3][N:4]([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([N:18]4[CH:23]=[CH:22][C:21]([C:24]5[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=5)=[CH:20][C:19]4=[O:34])=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 252058311-(1-(2-Morpholinoethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

Product 1

HCID 667191771-(1-(2-Morpholinoethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one hydrochlorideYield 69%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(1-(2-morpholinoethyl)-1H-indazol-5-yl)-4-(4-(trifluoro-methyl)-phenyl)pyridin-2(1H)-one (32 mg, 0.068 mmol) in CH2Cl2 (2 mL) was treated with anhydrous HCl in diethyl ether (0.07 mL, 0.07 mmol, 1.0 M). After stirring at ambient temperature for 15 min, the reaction mixture was diluted with Et2O (20 mL). The resulting solids were collected by filtration and dried in a vacuum oven to yield the title compound (24 mg, 69%) as an off-white powder: mp 248-250° C. (decomposition); 1H NMR (500 MHz, DMSO-d6) δ 10.58 (br s, 1H), 8.28 (s, 1H), 8.02 (d, J=8.0 Hz, 2H), 7.92-7.84 (m, 5H), 7.55 (d, J=9.0 Hz, 1H), 6.90 (d, J=2.0 Hz, 1H), 6.75 (dd, J=7.0, 2.0 Hz, 1H), 4.95 (br, 2H), 4.02-3.99 (m, 2H), 3.72-3.70 (m, 4H), 3.56-3.54 (m, 2H), 3.20 (br, 2H); ESI MS m/z 469 [M+H]+; HPLC (Method B) 98.9% (AUC), tR=14.8 min.

Workup

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

Sources & evidence

ORD record
ord-a2f68b6c18c242e4ba2edbb97a003ba2
Source dataset
uspto-grants-2012_09
Patent number
US08273770B2

Reaction notes

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