Glycolic Acid → HCID 59464215, compound

HRID 1713739Notes

Reaction equation

HRID 1713739 reaction equation
CCN=C=NCCCN(C)C.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]1[O:24][C:23]([C:25]([NH:27][C:28]2[CH:29]=[N:30][C:31]([N:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[O:26])=[N:22][N:21]=1.[C:40](O)(=[O:43])[CH2:41][OH:42].C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]1[O:24][C:23]([C:25]([NH:27][C:28]2[CH:29]=[N:30][C:31]([N:34]3[CH2:39][CH2:38][N:37]([C:41](=[O:42])[CH2:40][OH:43])[CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[O:26])=[N:22][N:21]=1

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59464054HCID 59464054, compound2×

Product 1

HCID 59464215HCID 59464215, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDAC (60 mg, 0.31 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), glycolic acid (20 mg (0.26 mmol) and HOBt (42 mg, 0.31 mmol) in 3 mL of DMF and stirring was continued for 16 h. Water (10 mL) was added and the resultant precipitate was collected by filtration, washed with water then ether and dried in vacuo to give the title compound (75 mg, 65%) as a solid; 1H NMR δ 10.94 (1H, s), 10.70 (1H, s), 8.50 (1H, s), 8.05 (1H, t), 7.90 (1H, d), 7.35-7.20 (2H, m), 7.20-7.10 (1H, m), 6.90 (1H, d), 4.60 (1H, t), 4.10 (2H, d), 3.60-3.4 (8H, m); MS m/e MH+ 442.

Workup

  1. filtrationthe resultant precipitate was collected by filtration
  2. washwashed with water
  3. dry with materialether and dried in vacuo

Sources & evidence

ORD record
ord-b8e3d44b10cf425293a481ce7f459fde
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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