Hydrochloric Acid → HCID 135978922, compound

HRID 17974Notes

Reaction equation

HRID 17974 reaction equation
N[N:2]1[C:7](=[O:8])[C:6]([CH:9]([NH:24][C:25]([CH:27]2[CH2:30][CH2:29][CH2:28]2)=[O:26])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:11]=2)=[N:5][N:4]=[CH:3]1.Cl.N([O-])=O.[Na+]>CCO.O>[CH2:17]([O:16][C:12]1[CH:11]=[C:10]([CH:9]([NH:24][C:25]([CH:27]2[CH2:28][CH2:29][CH2:30]2)=[O:26])[C:6]2[C:7](=[O:8])[NH:2][CH:3]=[N:4][N:5]=2)[CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 58592627HCID 58592627, compound

Product 1

HCID 135978922HCID 135978922, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of cyclobutanecarboxylic acid [(4-amino-5-oxo-4,5-dihydro-[1,2,4]triazin-6-yl)-(3-benzyloxy-phenyl)-methyl]-amide (315 mg, 0.777 mmol) and concentrated HCl (344 μL) in anhydrous EtOH (16 mL) was dropwise added a solution of sodium nitrite (120 mg, 1.72 mmol) in H2O (4 mL) at 0° C. and stirred for 30 min and warmed to rt for an additional 1.5 h. The reaction mixture was concentrated in vacuo and the crude material was chromatographed on silica gel [eluting with 3% MeOH in CHCl3] to obtain the title compound as an off-white foam solid. 1H NMR (CDCl3, 400 MHz) δ 1.78-1.93 (m, 1H), 1.93-2.04 (m, 1H), 2.12-2.2.36 (m, 4H), 3.13 (quint, J=8.4 Hz, 1H), 4.97 (s, 2H), 6.35 (d, J=8.8 Hz, 1H), 6.85 (dd, J=2.4, 8.4 Hz, 1H), 6.96-7.05 (m, 2H), 7.20 (t, J=8.0 Hz, 1H), 7.27-7.41 (m, 4H), 7.61 (brs, 1H), 8.46 (s, 1H); MS (ES+): m/z 391.04 (100) [MH+]; HPLC: tR=2.87 min (MicromassZQ, polar—5 min).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude material was chromatographed on silica gel [eluting with 3% MeOH in CHCl3]

Sources & evidence

ORD record
ord-f0a483427fa2485bb852ace4243a9a82
Source dataset
uspto-grants-2010_06
Patent number
US07741324B2

Reaction notes

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