Acetic Acid → HCID 59464141, compound

HRID 1713740Notes

Reaction equation

HRID 1713740 reaction equation
[O-:1][C:2]#[N:3].[Na+].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[O:17][C:16]([C:18]([NH:20][C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:25][CH:26]=2)=[O:19])=[N:15][N:14]=1.C(O)(=O)C.O1CCOCC1>O.C1COCC1>[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[O:17][C:16]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][N:30]([C:2]([NH2:3])=[O:1])[CH2:29][CH2:28]3)=[N:23][CH:22]=2)=[O:19])=[N:15][N:14]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 312751,4-DioxaneHCID 517096Sodium Cyanate2×HCID 59464054HCID 59464054, compound2×

Product 1

HCID 59464141HCID 59464141, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium cyanate 34 mg (0.52 mmol) was added to a mixture of 5-[(2-fluorophenyl)amino]-N-(6-piperazin-1-ylpyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide (Intermediate 41, 100 mg, 0.26 mmol) and glacial acetic acid (0.2 mL) in 0.6 mL of water (0.6 mL) and THF (0.3 mL). The mixture was stirred for 16 h then sodium cyanate (34 mg), glacial acetic acid (0.2 mL), dioxan (0.5 mL) and water (0.2 mL) were added. The mixture was stirred for another 2 h then directly purified by reverse phase HPLC, eluting with a gradient of acetonitrile/water containing 0.2% TFA, to give the title compound (90 mg, 82%) as a solid; 1H NMR δ 11.02 (1H, s), 10.74 (1H, s), 8.50 (1H, s), 8.05-7.95 (2H, m), 7.35-7.20 (2H, m), 7.20-7.10 (1H, m), 6.90 (1H, d), 3.60-3.4 (8H, m); MS m/e MH+ 427.

Workup

  1. stirringThe mixture was stirred for another 2 h
  2. customthen directly purified by reverse phase HPLC
  3. washeluting with a gradient of acetonitrile/water containing 0.2% TFA

Sources & evidence

ORD record
ord-26eafad6f94c46cead8d4321805d273a
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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