Diisopropylethylamine → (R)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(2-oxo-4-phenyl-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

HRID 501948Notes

Reaction equation

HRID 501948 reaction equation
[C:1](=O)([O:37]C1C=CC([N+]([O-])=O)=CC=1)[O:2][C@H:3]([CH2:18][C:19]1[CH:27]=[C:26]([CH3:28])[C:25]2[C:21](=[CH:22][N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[N:24]=2)[CH:20]=1)[C:4](=[O:17])[N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:7][CH2:6]1.[C:48]1([C:54]2[NH:55][C:56](=[O:65])[N:57]([CH:59]3[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]3)[CH:58]=2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[O:65]=[C:56]1[NH:55][C:54]([C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[CH:58][N:57]1[CH:59]1[CH2:60][CH2:61][N:62]([C:1]([O:2][C@H:3]([CH2:18][C:19]2[CH:27]=[C:26]([CH3:28])[C:25]3[C:21](=[CH:22][N:23]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:34])[CH3:36])[N:24]=3)[CH:20]=2)[C:4](=[O:17])[N:5]2[CH2:10][CH2:9][CH:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:7][CH2:6]2)=[O:37])[CH2:63][CH2:64]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 113455464-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-imidazol-2-oneHCID 59424375(R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-nitrophenyl carbonate

Product 1

HCID 59424328(R)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(2-oxo-4-phenyl-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-nitrophenyl carbonate (150 mg, 0.23 mmol) and 4-phenyl-(piperidin-4-yl)-1H-imidazol-2(3H)-one (PCT Int. Appl. 1998, WO 9811128 A1) (82.2 mg, 1.50 equiv) in dimethylformamide (1 mL) was added diisopropylethylamine (79 μL, 0.45 mmol) and stirred at room temperature overnight. The reaction was concentrated and purified by column chromatography to give 74 mg (43%) as a colorless film. Mass spec.: 770.57 (MH)+.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by column chromatography
  3. customto give 74 mg (43%) as a colorless film

Sources & evidence

ORD record
ord-1f905475d95346928baaa082bc13370d
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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