Hydrochloric Acid → HCID 69001366, compound

HRID 1909767Notes

Reaction equation

HRID 1909767 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][N:16]=1)=O)(C)(C)C.Cl>O1CCOCC1>[C:22]1([C:21]([C:18]2[CH:17]=[N:16][C:15]([O:14][CH2:13][C@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[CH:20][CH:19]=2)=[O:28])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68998680HCID 68998680, compound

Product 1

HCID 69001366HCID 69001366, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of product from step 3 (100 mg, 0.26 mmol) was treated with 5 ml of 4 N HCl in dioxane and stirred for 2 h. The solvent was removed in vacuo, triturated with ether to give the title compound as the hydrochloride salt (35 mg, 42%) MS; m/z 283 (M+H) 99%; 1H NMR (DMSO-d6, 400 MHz) δ 1.78-2.22 (4H, m), 3.20 (2H, m), 3.98 (1H, m), 4.45-4.65 (2H, m), 7.05 (1H, d, J=8.8 Hz), 7.60 (2H, m), 7.69-7.76 (3H, m), 8.14 (1H, dd, J1=2.8 Hz, J2=8.8 Hz), 8.56 (1H, dd, J1=0.8 Hz, J2=2.4 Hz), 9.2 (1NH, s)

Workup

  1. customThe solvent was removed in vacuo
  2. customtriturated with ether

Sources & evidence

ORD record
ord-a4f1eec0a1bd41b9b7d2358cf82444de
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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