Morpholine → HCID 57654472, compound

HRID 1921628Notes

Reaction equation

HRID 1921628 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[O:24][C:23]([CH:25]=O)=[CH:22][CH:21]=5)[CH:18]=[CH:19][C:14]4=[N:13][N:12]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C:11]3[N:15]4[N:16]=[C:17]([C:20]5[O:24][C:23]([CH2:25][N:27]6[CH2:32][CH2:31][O:30][CH2:29][CH2:28]6)=[CH:22][CH:21]=5)[CH:18]=[CH:19][C:14]4=[N:13][N:12]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 57654607HCID 57654607, compound

Product 1

HCID 57654472HCID 57654472, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

5-[3-(2,3-Dihydro-benzofuran-5-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]-furan-2-carbaldehyde (21.6 mg, 0.06 mmol), morpholine (6.5 μL, 0.07 mmol) and AcOH (2 drops) were combined in DCM (1 mL). To this was added sodium triacetoxyborohydride (19 mg, 0.09 mmol) and the reaction was stirred at rt for 2 hours. The reaction was concentrated in vacuo followed by purification by HPLC (5-65% CH3CN over 35 min) resulting in the title compound (5.9 mg, 27%) as a solid. 1H-NMR (CD3OD/CDCl3): δ 8.23-8.21 (1H, d, J=9.6 Hz), 7.81-7.78 (1H, d, J=9.8 Hz), 7.42-7.41 (1H, d, J=3.5 Hz), 7.22 (1H, s), 7.17-7.15 (1H, d, J=9.6 Hz), 6.99-6.98 (1H, d, J=3.5 Hz), 6.67-6.65 (1H, d, J=8.3 Hz), 4.57 (2H, s), 4.45-4.38 (4H, m), 3.94 (4H, br s), 3.40-3.33 (4H, m), 3.17-3.13 (2H, t, J=8.8 Hz). ESI-MS (m/z): Calcd. For C23H23N5O3: 417.18; found: 418.3 (M+H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customfollowed by purification by HPLC (5-65% CH3CN over 35 min)

Sources & evidence

ORD record
ord-984b3c02b6ff4552ab27eda97b89d996
Source dataset
uspto-grants-2012_05
Patent number
US08173654B2

Reaction notes

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