Hydrochloric Acid → HCID 69978083, compound

HRID 2302011Notes

Reaction equation

HRID 2302011 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][N:3]=[C:2]1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH:17]([CH2:22][C:23]([OH:25])=[O:24])[CH2:16][CH2:15]2.[ClH:26].[CH3:27]COCC>CO>[ClH:26].[ClH:26].[CH3:27][O:24][C:23](=[O:25])[CH2:22][CH:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][CH2:10][CH2:9][CH2:8][NH:7][C:2]3[NH:3][CH2:4][CH2:5][CH2:6][N:1]=3)[CH:13]=2)[CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 18462609HCID 18462609, compound

Product 1

HCID 69978083HCID 69978083, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of {6-[3-(1,4,5,6-tetrahydro-pyrimidin-2-ylamino)-propoxy]-1,2,3,4-tetrahydro-naphthalen-2-yl}-acetic acid (25 mg) in MeOH (2 mL) was added HCl in MeOH and the solution was heated to reflux for 3 h. The reaction was cooled to room temperature and concentrated under reduced pressure to afford a tan oil. Ether was added, the contents were swirled and the solvent decanted. Lyophilization of the oily residue gave the title compound as a hygroscopic, ivory solid (29 mg). NMR (300 MHz, MeOH-d4) δ6.84 (d, J 8.20 Hz, 1H), 6.61-6.56 (m, 2H), 3.92 (t, J=5.75 Hz, 2H), 3.59 (s, 3H), 3.28-3.21 (m, 5H), 2.72-2.68 (m, 3H), 2.33-2.24 (m, 3H), 2.09-2.06 (m, 1H), 1.92 (t, J=7.09 Hz, 2H), 1.87-1.77 (m, 3H), 1.37-1.19 (m, 2H); MS (+ESI) m/z 360 (M+H)+; Calculated for C20H29N3O3.2 HCl: C, 55.56; H, 7.23; N, 9.72. Found: C, 55.15; H. 7.10; N, 9.88.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated under reduced pressure
  4. customto afford a tan oil
  5. customthe solvent decanted

Sources & evidence

ORD record
ord-5f39ad10317a4498bc463fc7b9422965
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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