Diisopropylethylamine → HCID 178490379, compound

HRID 333429Notes

Reaction equation

HRID 333429 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].C1([C:38]2([C:44]([OH:46])=[O:45])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)CCCCC1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=N[C:66]2[CH:67]=[CH:68][CH:69]=[CH:70][C:65]1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C)C=O.O>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH:65]1([CH:40]2[CH2:39][CH:38]([C:44]([OH:46])=[O:45])[CH2:43][CH2:42][N:41]2[C:12](=[O:14])[CH:11]([NH:10][C:9]([NH:8][CH2:7][CH2:6][C:4]2[N:3]=[CH:2][NH:1][CH:5]=2)=[O:24])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 669876094-Cyclohexyl-piperidine-4-carboxylic acid trifluoroacetateHCID 178490381HCID 178490381, compound

Product 1

HCID 178490379HCID 178490379, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution containing 93 mg (0.28 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propanoic acid and 100 mg (0.31 mmol) of 4-cyclohexyl-piperidine-4-carboxylic acid trifluoroacetate in 0.8 mL of dimethylformamide are added 0.16 mL of diisopropylethylamine and 90 mg (0.28 mmol) of TBTU. The reaction medium is stirred at room temperature for 18 hours. The reaction is stopped by adding water, and the organic compounds are extracted with dichloromethane. The organic phase is dried and evaporated. The oil obtained is purified by preparative HPLC (conditions cf. page 38). 35 mg of cyclohexyl-1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]piperidine-4-carboxylic acid trifluoroacetate are obtained in a yield of 19%.

Workup

  1. extractionthe organic compounds are extracted with dichloromethane
  2. customThe organic phase is dried
  3. customevaporated
  4. customThe oil obtained
  5. customis purified by preparative HPLC (conditions cf. page 38)

Sources & evidence

ORD record
ord-a934281c0c5c491eb36ce7a802c85b1a
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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