Phenylacetic Acid → HCID 68709488, compound

HRID 889317Notes

Reaction equation

HRID 889317 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]1([CH2:29][C:30](O)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>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:30](=[O:31])[CH2:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[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

7

Reactant 5

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68704213HCID 68704213, compound

Product 1

HCID 68709488HCID 68709488, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

80.0 mg (235 μmol) of the compound from Example 35 and 35.2 mg (259 μmol) phenylacetic acid are dissolved in 5 ml DMF, 119 mg (1.18 mmol) triethylamine, 90.2 mg (470 μmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 127 mg (941 μmol) 1-hydroxy-1H-benzotriazole hydrate are added, while cooling with ice, and the mixture is stirred overnight at RT. The precipitate is filtered off and the filtrate is purified 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. filtrationThe precipitate is filtered off
  3. customthe filtrate is purified 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-bf06bff147a9450da7644a506c0aa272
Source dataset
uspto-grants-2012_08
Patent number
US08252817B2

Reaction notes

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