Triethylamine → HCID 58431113, compound

HRID 1040543Notes

Reaction equation

HRID 1040543 reaction equation
[C:1]([CH2:4][CH2:5][C@H:6]([NH:10][C:11]([C:13]1[N:17]2[C@@:18]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=3)([CH3:30])[C:19](=[O:29])[N:20]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)[C:16]2=[N:15][CH:14]=1)=[O:12])[C:7](O)=[O:8])(=[O:3])[NH2:2].Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.[NH:69]1[CH2:74][CH2:73][CH2:72][CH:71]([C:75]([NH2:77])=[O:76])[CH2:70]1>CN(C=O)C.O>[NH2:2][C:1](=[O:3])[CH2:4][CH2:5][C@H:6]([NH:10][C:11]([C:13]1[N:17]2[C@@:18]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([C:38]#[N:39])=[CH:36][CH:37]=3)([CH3:30])[C:19](=[O:29])[N:20]([C:21]3[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=3)[C:16]2=[N:15][CH:14]=1)=[O:12])[C:7]([N:69]1[CH2:74][CH2:73][CH2:72][CH:71]([C:75](=[O:76])[NH2:77])[CH2:70]1)=[O:8]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 929803-PiperidinecarboxamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58431022HCID 58431022, compound

Product 1

HCID 58431113HCID 58431113, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-4-carbamoyl-2-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-butyric acid (50 mg, 0.088 mmol) in DMF (1 mL) was added (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (25 mg, 0.132 mmol), benzotriazol-1-ol (18 mg, 0.132 mmol) and triethylamine (47 μL, 0.395 mmol). The reaction mixture was stirred at room temperature for 20 min then piperidine-3-carboxylic acid amide (17 mg, 0.132 mmol) was added. The reaction mixture was stirred at room temperature for 64 h. The reaction mixture was then diluted with water and filtered through a glass frit. The solution was then extracted with CH2Cl2 (×3). The combined organic layers were then washed with water (×3). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified via reverse phase HPLC to afford 60 mg of the title compound as a white solid, m/z 679.6 [M+1]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 64 h
  2. filtrationfiltered through a glass frit
  3. extractionThe solution was then extracted with CH2Cl2 (×3)
  4. washThe combined organic layers were then washed with water (×3)
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified via reverse phase HPLC

Sources & evidence

ORD record
ord-9440cc8845e84589bf97983c72ed74bc
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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