Ammonia → HCID 70083023, compound

HRID 1416658Notes

Reaction equation

HRID 1416658 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)(OC(C)(C)C)=O.[ClH:22].N.CO>C(O)C>[ClH:22].[ClH:22].[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric Acid2×HCID 887MethanolHCID 21309677HCID 21309677, compound

Product 1

HCID 70083023HCID 70083023, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of the compound from step 102b above (60 mg, 0.20 mmol) in 3 mL of ethanol at Q20 C was added saturated HCl in ethanol (10 mL), and the reaction mixture was stirred for 30 minutes at 0° C. The volatiles were removed under vacuum, and the residue was purified on a column of silica gel, eluting with methanol/methylene chloride (5:95). The product was treated with a saturated solution of HCl/EtOH and held under vacuum for 24 hours to afford a white solid. MS (DCI/NH3) m/e: 193 (M+H)+, 210 (M+NH4)+. 1H NMR (D2O, 300 MHz) δ: 1.69-1.86 (m, 1H), 1.91-2.20 (m, 3H), 2.26-2.43 (m, 2H), 3.28-3.47 (m, 2H), 3.70-3.85 (m, 1H), 4.27-4.45 (m, 2H), 7.82 (dd, J_8.5, 5.0 Hz, 1H), 7.98 (dd, J=9.0, 4.0 Hz, 1H), 8.35 (d, J=6.0 Hz, 1H), 8.45 (d, J=2.0 Hz, 1H). Anal. Calc. for C11H16N2O·2.3 HCl: C, 47.84; H, 6.68; N, 10.14; Found C, 47.48; H. 6.92; N, 9.94. [α]25D =+41.62° (c=0.41, methanol).

Workup

  1. customThe volatiles were removed under vacuum
  2. customthe residue was purified on a column of silica gel
  3. washeluting with methanol/methylene chloride (5:95)
  4. additionThe product was treated with a saturated solution of HCl/EtOH
  5. waitheld under vacuum for 24 hours
  6. customto afford a white solid

Sources & evidence

ORD record
ord-aed2457b5d2e4409a8eac3bb217602ed
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

Loading…