Butyric Acid → HCID 68706771, compound

HRID 889310Notes

Reaction equation

HRID 889310 reaction equation
[ClH:1].Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[C:15](=[O:16])[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][NH:12]2)[CH:6]=1.[C:23](O)(=[O:27])[CH2:24][CH2:25][CH3:26].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[ClH:1].[O:16]=[C:15]1[N:11]([C:7]2[CH:6]=[C:5]([CH2:4][NH:3][C:23](=[O:27])[CH2:24][CH2:25][CH3:26])[CH:10]=[CH:9][N:8]=2)[NH:12][CH:13]=[C:14]1[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 264Butyric AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68704213HCID 68704213, compound

Product 1

HCID 68706771HCID 68706771, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80.0 mg (235 μmol) of the compound from Example 35 and 22.8 mg (259 μmol) butyric acid are dissolved in 5 ml DMF, 119 mg (1.18 mmol) triethylamine and 90.2 mg (470 μmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride are added, while cooling with ice, and the mixture is stirred overnight at RT. The reaction mixture is then purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% conc. hydrochloric acid).

Workup

  1. temperaturewhile cooling with ice
  2. customThe reaction mixture is then purified directly by means of preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% conc. hydrochloric acid)

Sources & evidence

ORD record
ord-8c037b5217574dd0b06057183d8b2adf
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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