Dimethylformamide → HCID 136334024, compound

HRID 2089626Notes

Reaction equation

HRID 2089626 reaction equation
C(O)(=O)C.[F:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][C:9]([O:16][CH3:17])=[CH:8][C:7]=1[CH:18]([NH:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([NH2:38])=[NH:37])=[CH:34][CH:33]=1)[C:19]1[NH:23][C:22](=[O:24])[N:21]([C:25]2[N:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:20]=1.CN(C=O)C.[N+](C1C=CC([O:55][C:56](=O)[O:57][CH2:58][C:59]([CH3:62])([CH3:61])[CH3:60])=CC=1)([O-])=O.C(N(CC)CC)C>C(O)(=O)C>[CH3:60][C:59]([CH3:62])([CH3:61])[CH2:58][O:57][C:56](=[O:55])[N:37]=[C:36]([NH2:38])[C:35]1[CH:34]=[CH:33][C:32]([NH:31][CH:18]([C:7]2[CH:8]=[C:9]([O:16][CH3:17])[CH:10]=[C:11]([O:12][CH2:13][CH2:14][OH:15])[C:6]=2[F:5])[C:19]2[NH:23][C:22](=[O:24])[N:21]([C:25]3[N:26]=[CH:27][CH:28]=[CH:29][N:30]=3)[N:20]=2)=[CH:40][CH:39]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 22389509Carbonic acid 2,2-dimethylpropyl ester 4-nitrophenyl esterHCID 1363340234-({[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl}amino)benzamidine acetic acid salt

Product 1

HCID 136334024HCID 136334024, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 4-({[2-fluoro-3-(2-hydroxyethoxy)-5-methoxyphenyl]-(5-oxo-1-pyrimidin-2-yl-4,5-dihydro-1H-[1,2,4]triazol-3-yl)methyl}amino)benzamidine acetic acid salt (6 g) and DMF (500 mL), carbonic acid 2,2-dimethylpropyl ester 4-nitrophenyl ester [CAS No. 158810-98-1] (3.06 g) and triethylamine (4.64 mL) were added, and the resulting mixture was stirred overnight at room temperature. Acetic acid (5 mL) was added to the reaction solution, and the solvent was evaporated under reduced pressure. The residue obtained was purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate) to obtain the captioned compound (6.5 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue obtained
  3. customwas purified by NAM silica gel column chromatography (mixed solvent of methanol-ethyl acetate)

Sources & evidence

ORD record
ord-eeee7642280c481f937ef8f4c8be72c3
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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