Hydrochloric Acid → HCID 68705774, compound

HRID 2242874Notes

Reaction equation

HRID 2242874 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:27]([Cl:28])=[C:26]3[C:21]([CH:22]=[CH:23][CH:24]=[CH:25]3)=[N:20]2)=[CH:15][CH:14]=1.O.Cl>O1CCOCC1>[ClH:28].[Cl:28][C:27]1[N:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C@H:7]3[CH2:8][CH2:9][CH2:10][N:6]3[CH2:5][CH2:4][C:3]([OH:29])=[O:2])=[CH:14][CH:15]=2)[N:20]=[C:21]2[C:26]=1[CH:25]=[CH:24][CH:23]=[CH:22]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68704344HCID 68704344, compound

Product 1

HCID 68705774HCID 68705774, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of step 1 (0.37 g, 0.89 mmol), water (1 mL) and HCl (4 M in dioxane, 2.3 mL, 9.1 mmol) in dioxane (5 mL) was stirred at room temperature for 16 h. After the solvent was removed, the residue was triturated with ether to provide the title compound (200 mg, 44%) as a hydrochloride salt. 1H NMR (400 MHz, CDCl3) δ 7.72-7.66 (m, 4H), 7.41 (m, 1H), 7.23 (m, 3H), 4.44 (br, 2H), 4.03 (br, 1H), 3.71 (br, 2H), 3.35 (br, 1H), 3.20 (br, 1H), 2.87 (t, J=8 Hz, 2H), 2.27 (m, 1H), 2.09-1.98 (br, 3H), LC/MS (APCI) m/z: 85%.

Workup

  1. customAfter the solvent was removed
  2. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-c62dbbd3d32d430cb842a941622c0620
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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