Triethylamine → HCID 66558504, compound

HRID 1530512Notes

Reaction equation

HRID 1530512 reaction equation
[CH2:1]1[NH:6][CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:2]12.CCN(CC)CC.[CH:18]([N:21]1[C:25]([C:26]2[N:35]=[C:34]3[N:28]([CH2:29][CH2:30][O:31][C:32]4[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][C:33]=43)[CH:27]=2)=[N:24][CH:23]=[N:22]1)([CH3:20])[CH3:19]>C(Cl)Cl>[CH2:1]1[N:6]([S:40]([C:37]2[CH:38]=[CH:39][C:32]3[O:31][CH2:30][CH2:29][N:28]4[CH:27]=[C:26]([C:25]5[N:21]([CH:18]([CH3:19])[CH3:20])[N:22]=[CH:23][N:24]=5)[N:35]=[C:34]4[C:33]=3[CH:36]=2)(=[O:42])=[O:41])[CH2:5][CH2:4][N:3]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:2]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2876391(+-)-1,4-Diazabicyclo[4.4.0]decaneHCID 86671461HCID 86671461, compound

Product 1

HCID 66558504HCID 66558504, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of octahydropyrido[1,2-a]pyrazine (50 mg, 0.38 mmol) and NEt3 (83 μL, 0.59 mmol) in DCM (15 mL) at 0° C. was added a suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonyl chloride from Example 121 (93 mg, 0.12 mmol) in DCM (5 mL) and the resulting mixture warmed to RT after 10 min then stirred for 1 h. The reaction mixture was diluted with DCM, washed with a saturated aqueous NaHCO3 solution then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% MeOH in EtOAc) then freeze-dried from MeCN/H2O affording 132 (36 mg, 62%) as a white solid. LCMS: RT 2.90 min [M+H]+ 498.3. 1H NMR (DMSO, 400 MHz): δ 8.78 (1H, d, J=2.41 Hz), 8.01 (1H, s), 7.94 (1H, s), 7.63 (1H, dd, J=8.63, 2.42 Hz), 7.28 (1H, d, J=8.62 Hz), 5.73-5.72 (1H, m), 4.63-4.59 (4H, m), 3.53 (1H, d, J=11.02 Hz), 3.43 (1H, d, J=9.07 Hz), 2.70-2.68 (2H, m), 2.33-2.32 (1H, m), 2.19-2.11 (1H, m), 1.93-1.92 (3H, m), 1.62 (1H, d, J=12.59 Hz), 1.57-1.52 (2H, m), 1.49 (6H, t, J=6.30 Hz), 1.38-1.16 (2H, m), 1.01-0.87 (1H, m)

Workup

  1. washwashed with a saturated aqueous NaHCO3 solution
  2. dry with materialthen dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-8% MeOH in EtOAc)
  5. dry with materialthen freeze-dried from MeCN/H2O affording 132 (36 mg, 62%) as a white solid

Sources & evidence

ORD record
ord-076ff4be325547808847c7a0a3b6da90
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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