Dimethylformamide → HCID 11758202, compound

HRID 1835610Notes

Reaction equation

HRID 1835610 reaction equation
[NH2:1][CH:2]([C:7](=[O:36])[NH:8][CH2:9][C:10]([CH3:35])([CH3:34])[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[C:18]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:17]=1)[CH2:3][C:4]([OH:6])=[O:5].CN(C)C=O.C(N(CC)CC)C.[C:49](ON1C(=O)CCC1=O)(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[N:52][CH:51]=1>C(#N)C.O>[C:22]1([C:20]2[CH:19]=[C:18]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:17]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([CH3:34])([CH3:35])[CH2:9][NH:8][C:7]([CH:2]([NH:1][C:49]([C:50]3[CH:51]=[N:52][CH:53]=[CH:54][CH:55]=3)=[O:56])[CH2:3][C:4]([OH:6])=[O:5])=[O:36])[CH:21]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 870586Succinimidyl NicotinateHCID 23501871HCID 23501871, compound

Product 1

HCID 11758202HCID 11758202, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of 3-amino-3-(N-(6-(4,6-diphenyl(2-pyridyloxy))-2,2-dimethylhexyl)carbamoyl)propanoic acid (100 mg, 0.204 mmol), N,N-dimethylformamide (2 mL), and triethylamine (0.1 mL) was stirred at room temperature for 5 min. Succinimidyl nicotinate (69 mg, 0.315 mmol) was added, and the mixture was stirred for 18 h. The mixture was concentrated under high vacuum, and the residue was purified using reverse-phase HPLC (water-acetonitrile gradient containing 0.1% TFA) to afford 23 mg (19%) of a white powdered solid. ESMS: Calculated for C35H38N4O5, 594.2842 Found 595.2 [M+H]+1; Rt=15.597 min (100% pure, Vydac C18 column; gradient 20 to 100% acetonitrile/water+0.1% TFA over 30 min).

Workup

  1. stirringthe mixture was stirred for 18 h
  2. concentrationThe mixture was concentrated under high vacuum
  3. customthe residue was purified
  4. additionreverse-phase HPLC (water-acetonitrile gradient containing 0.1% TFA)
  5. customto afford 23 mg (19%) of

Sources & evidence

ORD record
ord-beda92efcac54659b9eab6eab776a959
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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