Phenyl isocyanate → HCID 59464103, compound

HRID 1713741Notes

Reaction equation

HRID 1713741 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]1[O:22][C:21]([C:23]([NH:25][C:26]2[CH:27]=[N:28][C:29]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:30][CH:31]=2)=[O:24])=[N:20][N:19]=1>CN(C=O)C>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]1[O:22][C:21]([C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][N:35]([C:8]([NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[O:9])[CH2:34][CH2:33]3)=[N:28][CH:27]=2)=[O:24])=[N:20][N:19]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 59464054HCID 59464054, compound2×

Product 1

HCID 59464103HCID 59464103, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl isocyanate (0.032 mL, 0.29 mmol) was added to a stirred 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 DMF (1.5 mL). After 2 h the crude reaction mixture was directly purified by reverse phase HPLC eluting with a gradient of acetonitrile/water containing 0.2% TFA to give the title compound (28 mg, 20%) as a solid; 1H NMR δ 11.00 (1H, s), 10.74 (1H, s), 8.55 (1H, s), 8.50 (1H, s), 8.05-7.95 (2H, m), 7.45 (2H, d), 7.35-7.10 (4H, m), 7.00 (1H, d), 6.90 (1H, t), 3.80-3.60 (8H, m); MS m/e MH+ 503.

Workup

  1. customAfter 2 h the crude reaction mixture
  2. customwas directly purified by reverse phase HPLC
  3. washeluting with a gradient of acetonitrile/water containing 0.2% TFA

Sources & evidence

ORD record
ord-7378309bf3bb4f02b54539965e717227
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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