Diisopropylethylamine → 3-(1-Cyclopropyl-isoquinoline-3-carbonyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester

HRID 334025Notes

Reaction equation

HRID 334025 reaction equation
[CH:1]1([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:7]=[C:6]([C:14]([OH:16])=O)[N:5]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[CH2:24]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][C:35]1([CH3:41])[CH3:40])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:24]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH:36]([C:14]([C:6]2[N:5]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)=[O:16])[C:35]1([CH3:41])[CH3:40])=[O:33])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866882432,2-Dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetateHCID 866882551-Cyclopropyl-isoquinoline-3-carboxylic acid

Product 1

HCID 866882563-(1-Cyclopropyl-isoquinoline-3-carbonyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

230 mg (1.08 mmol) 1-cyclopropyl-isoquinoline-3-carboxylic acid and 391 mg (1.08 mmol) 2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate was stirred with 385 mg (1.20 mmol) TBTU and 640 μL (3.70 mmol) DIPEA in 3 mL DMF at RT for 1 h. The mixture was worked up by adding water, followed by extraction with EtOAc. Then the reaction mixture was washed with saturated aqueous NaHCO3 solution. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. Yield: 600 mg (99%), purity: 80%; ESI-MS: m/z=444 (M+H)+; Rt(HPLC): 1.42 min (method 5)

Workup

  1. extractionfollowed by extraction with EtOAc
  2. washThen the reaction mixture was washed with saturated aqueous NaHCO3 solution
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3d409b280a9430ea0d83a2052ed9e82
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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