Ammonia → HCID 21309667, compound

HRID 1416606Notes

Reaction equation

HRID 1416606 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:8][O:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH3:2].[ClH:16].N.CO>C(OCC)C>[ClH:16].[ClH:16].[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C@H:4]1[CH2:8][O:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH3:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 887MethanolHCID 21309668HCID 21309668, compound

Product 1

HCID 21309667HCID 21309667, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The free base from step 38b was dissolved in diethyl ether and brought to 0° C. with stirring. The solution was treated with diethyl ether saturated with HCl. The solvent was removed in vacuo. The resulting salt was triturated with diethyl ether (2×) and dried under vacuum to give a white powder. MS (DCI/NH3) m/e207 (M+H)+. 1H NMR (D2O,300 MHz) δ: 8.49 (d, J=3.0 Hz, 1H), 8.39 (dd, J=1.0,5.1 Hz, 1H), 8.02 (m, 1H), 7.85 (dd, J=8.70, 5.40 Hz, 1H), 4.61 (dd, J=11.0, 3.3 Hz, 1H), 4.44 (dd, J=11.0, 6.6 Hz, 1H), 4.10-4.01 (m, 1H), 3.79-3.72 (m, 1H), 3.65-3.51 (m, 2H), 3.32-3.18 (m, 2H), 2.44-2.33 (m, 1H), 2.27-2.05 (m, 2H), 1.37 (t, J=7.5 Hz, 3H). Anal. Calc. for C12H18N2OΩ2.0 HCl: C, 51.57; H, 7.16; N, 10.02; Found C, 51.43; H, 7.39; N, 9.96. [α]D =-1.5° (c 0.46, MeOH).

Workup

  1. custombrought to 0° C.
  2. customThe solvent was removed in vacuo
  3. customThe resulting salt was triturated with diethyl ether (2×)
  4. customdried under vacuum
  5. customto give a white powder

Sources & evidence

ORD record
ord-dc2518b7ab9842fd944c0269f56e8648
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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