Dimethylacetamide → HCID 59529487, compound

HRID 1877287Notes

Reaction equation

HRID 1877287 reaction equation
[CH:1]1([CH:7]([C:18]2[C:22]([CH3:23])=[CH:21][N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=3)[CH:19]=2)[O:8][C:9]2[CH:17]=[CH:16][C:12](C(O)=O)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.[NH2:35][CH2:36][CH2:37][C:38]([O:40]CC)=[O:39].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C[C:67](N(C)C)=[O:68]>O.C(N(CC)CC)C>[CH:1]1([CH:7]([C:18]2[C:22]([CH3:23])=[CH:21][N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:31])[F:32])[CH:25]=3)[CH:19]=2)[O:8][C:9]2[CH:17]=[CH:16][C:12]([C:67]([NH:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[O:68])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 31374DimethylacetamideHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68513427HCID 68513427, compound

Product 1

HCID 59529487HCID 59529487, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution (10 mL) of 4-(cyclohexyl{4-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrol-3-yl}methoxy)benzoic acid (0.43 g) synthesized in Example 300 (1) in dimethylacetamide were added triethylamine (0.14 mL), ethyl 3-aminopropanoate hydrochloride (0.16 g), N-(3-dimethylaminopropyl)-ethylcarbodiimide hydrochloride (0.29 g) and 1-hydroxybenzotriazole monohydrate (0.23 g) at room temperature, and the mixture was stirred at 60° C. for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate and purified by silica gel chromatography (ethyl acetate:hexane=1:1, volume ratio) to give a methyl ester form of the title compound (0.10 g). This was dissolved in ethanol (2 mL), 1N sodium hydroxide (1.5 mL) was added, and the mixture was stirred at room temperature for 1 hr. Ethanol was evaporated under reduced pressure, and 1N hydrochloric acid (1.5 mL) was added to the residue to give the title compound (25.4 mg, 5%) as an amorphous form.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. custompurified by silica gel chromatography (ethyl acetate:hexane=1:1, volume ratio)

Sources & evidence

ORD record
ord-e0bc15702da547cabc192a8edf7fd232
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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