Hydrochloric Acid → HCID 68457435, compound

HRID 2387480Notes

Reaction equation

HRID 2387480 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][CH2:29][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][CH2:29][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 25057642HCID 25057642, compound

Product 1

HCID 68457435HCID 68457435, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(benzyloxy)-1-(1-(2-(piperidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (26.7 mg, 0.062 mmol) in CH2Cl2 (0.3 mL) was treated with anhydrous HCl in diethyl ether (62 μL, 0.062 mmol, 1.0 M). After stirring at ambient temperature for 2.0 h, the solids were collected by filtration, washed with diethyl ether and dried to yield the title compound (22.8 mg, 78%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 9.85 (br s, 1H), 8.24 (s, 1H), 7.85 (d, J=9.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.48-7.36 (m, 6H), 6.12 (dd, J=7.5, 3.0 Hz, 1H), 5.99 (d, J=3.0 Hz, 1H), 5.15 (s, 2H), 4.89 (t, J=6.5 Hz, 2H), 3.61-3.54 (m, 4H), 3.00-2.94 (m, 2H), 1.84-1.81 (m, 2H), 1.68-1.65 (m, 3H), 1.41-1.36 (m, 1H); ESI MS m/z 429 [M+H]+; HPLC (Method A) 99.5% (AUC), tR=14.2 min.

Workup

  1. filtrationthe solids were collected by filtration
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-da8d6e0900db4dc2a4e1d3f3a703771f
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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