Formaldehyde → HCID 49764679, compound

HRID 2279218Notes

Reaction equation

HRID 2279218 reaction equation
C=O.[O:3]=[C:4]1[NH:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[N:7]2[CH2:15][CH2:16][N:17]([C:19](OC(C)(C)C)=O)[CH2:18][CH:6]2[CH2:5]1>C(O)=O>[CH3:19][N:17]1[CH2:16][CH2:15][N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[NH:10][C:4](=[O:3])[CH2:5][CH:6]2[CH2:18]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 58284919tert-butyl 6-oxo-1,2,4a,5,6,7-hexahydropyrazino[1,2-a][1,5]benzodiazepine-3(4H)-carboxylate

Product 1

HCID 49764679HCID 49764679, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Formalin solution (0.3 mL, 3.92 mmol) was added to a solution of the product of Example 22D (150 mg, 0.473 mmol) in 88% formic acid (4 mL), and the solution was stirred at 100° C. under nitrogen for 30 minutes. The mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by chromatography (SiO2, eluted with CH2Cl2-methanol-15 M NH4OH, 90:10:1) to provide the title compound: 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 2.05 (d, J=12.8 Hz, 1H), 2.66 (dd, J=13.6, 7.2 Hz, 1H), 2.90 (s, 3H), 3.08-3.19 (m, 2H), 3.32-3.39 (m, 2H), 3.53 (t, J=11.0 Hz, 2H), 3.57-3.67 (m, 1H), 7.00-7.04 (m, 1H), 7.08-7.13 (m, 1H), 7.13-7.18 (m, 1H), 7.18-7.24 (m, 1H); MS (DCI) m/z 232 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by chromatography (SiO2, eluted with CH2Cl2-methanol-15 M NH4OH, 90:10:1)

Sources & evidence

ORD record
ord-9cd0d9bf442d44b68be05b62a30c4f27
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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