Water → HCID 57518501, compound

HRID 38461Notes

Reaction equation

HRID 38461 reaction equation
C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[O:13]=[C:14]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:29]3[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][N:30]=3)[CH:27]=2)[O:22][C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:15]1.[CH2:38]([O:40][C:41]1[CH:46]=[C:45]([C:47](O)=[O:48])[CH:44]=[C:43]([O:50][CH2:51][CH3:52])[C:42]=1[C:53]1[CH:58]=[CH:57][C:56]([C:59]([O:61][CH3:62])=[O:60])=[CH:55][CH:54]=1)[CH3:39].O>CN(C=O)C>[C:33]([C:32]1[CH:36]=[CH:37][C:29]([C:26]2[CH:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[O:22][C:16]2([CH2:21][CH2:20][N:19]([C:47]([C:45]4[CH:44]=[C:43]([O:50][CH2:51][CH3:52])[C:42]([C:53]5[CH:58]=[CH:57][C:56]([C:59]([O:61][CH3:62])=[O:60])=[CH:55][CH:54]=5)=[C:41]([O:40][CH2:38][CH3:39])[CH:46]=4)=[O:48])[CH2:18][CH2:17]2)[CH2:15][C:14]3=[O:13])=[N:30][CH:31]=1)(=[O:34])[NH2:35]

Participants

6

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 667818846-(4-Oxospiro[chroman-2,4'-piperidin]-6-yl)nicotinamide dihydrochlorideHCID 670555482,6-Diethoxy-4'-(methoxycarbonyl)biphenyl-4-carboxylic acid

Product 1

HCID 57518501HCID 57518501, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

TEA (0.657 ml, 4.71 mmol) was added to a stirred mixture of HOBT (313 mg, 2.04 mmol), WSCDI (361 mg, 1.89 mmol), 6-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)nicotinamide dihydrochloride (2.61 g, 6.97 mmol) and 2,6-diethoxy-4′-(methoxycarbonyl)biphenyl-4-carboxylic acid (2.00 g, 5.81 mmol) in DMF (30 ml) and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into water (600 ml) and stirred for 30 min. The resulted precipitate was filtered, washed with water and the solid was dried in vacuo at 70° C. The crude product was purified by silicagel column chromatography (CHCl3/Acetone) to give intended compound (3.85 g, quantitative) as a colorless solid.

Workup

  1. stirringstirred for 30 min
  2. filtrationThe resulted precipitate was filtered
  3. washwashed with water
  4. customthe solid was dried in vacuo at 70° C
  5. customThe crude product was purified by silicagel column chromatography (CHCl3/Acetone)
  6. customto give intended compound (3.85 g, quantitative) as a colorless solid

Sources & evidence

ORD record
ord-e3c7a1cafabd4e63a22d3aa0c13d5b16
Source dataset
uspto-grants-2013_09
Patent number
US08524730B2

Reaction notes

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