1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-N-(1-(2-(tert-butyldimethylsilyloxy)ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

HRID 747055Notes

Reaction equation

HRID 747055 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[C@@H:3]1[CH2:18][C:19](O)=[O:20].[Si:22]([O:29][CH2:30][CH2:31][N:32]1[C:40]2[CH2:39][CH2:38][CH2:37][CH:36]([NH2:41])[C:35]=2[CH:34]=[N:33]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[Si:22]([O:29][CH2:30][CH2:31][N:32]1[C:40]2[CH2:39][CH2:38][CH2:37][CH:36]([NH:41][C:19](=[O:20])[CH2:18][C@@H:3]3[C:2](=[O:1])[NH:7][CH2:6][CH2:5][N:4]3[S:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:15])=[CH:16][CH:17]=3)(=[O:10])=[O:9])[C:35]=2[CH:34]=[N:33]1)([C:25]([CH3:28])([CH3:26])[CH3:27])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 33736624(R)-2-(3-oxo-1-tosylpiperazin-2-yl)acetic acidHCID 597479321-(2-(Tert-butyldimethylsilyloxy)ethyl)-4,5,6,7-tetrahydro-1h-indazol-4-ylamine

Product 1

HCID 69075580(R)-N-(1-(2-(tert-butyldimethylsilyloxy)ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl)-2-(3-oxo-1-tosylpiperazin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (R)-2-(3-oxo-1-tosylpiperazin-2-yl)acetic acid (624 mg, 2.0 mmol), 1-(2-(tert-butyldimethylsilyloxy)ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-amine (649 mg, 2.2 mmol), HOBt (297 mg, 2.2 mmol) and EDCI (422 mg, 2.2 mmol) in 1.2 mL of DMF was stirred overnight at room temperature. After quenching with Sat. NaHCO3 solution, the reaction mixture was extracted with EtOAc. The combined organic phase was washed brine, dried over Na2SO4, and evaporated in vaco. Flash chromatography (SiO2, EtOAc/MeOH=100:4 to 100:8 to 100:10 to 100:15) gave the title compound as a white solid. MS: 590.2 (M+1).

Workup

  1. customAfter quenching with Sat. NaHCO3 solution
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washThe combined organic phase was washed brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vaco

Sources & evidence

ORD record
ord-c6d7323ba80a46b388fd52f1337b6d99
Source dataset
uspto-grants-2008_07
Patent number
US07393852B2

Reaction notes

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