Diisopropylethylamine → HCID 68760982, compound

HRID 79588Notes

Reaction equation

HRID 79588 reaction equation
Cl.Cl.[C:3]1([C:9]2[C:10]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([C@@H:35]2[CH2:39][CH2:38][C:37]([CH3:41])([CH3:40])[N:36]2[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:32](O)=[O:33])=[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>C(Cl)Cl>[Br:24][C:25]1[CH:26]=[CH:27][C:28]([C@@H:31]([C@H:35]2[N:36]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[C:37]([CH3:41])([CH3:40])[CH2:38][CH2:39]2)[C:32](=[O:33])[N:21]2[CH2:20][CH2:19][N:18]([C:10]3[C:9]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=4)=[CH:14][N:13]=[C:12]4[NH:15][CH:16]=[CH:17][C:11]=34)[CH2:23][CH2:22]2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59564917(S)-2-(4-bromophenyl)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)acetic acidHCID 687587805-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine dihydrochloride

Product 1

HCID 68760982HCID 68760982, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyri dine dihydrochloride (0.0159 g, 0.0454 mmol, see Example 19), (S)-2-(4-bromophenyl)-2-((S)-1-(tert-butoxycarbonyl)-5,5-dimethylpyrrolidin-2-yl)acetic acid (0.017 g, 0.0412 mmol, see Example C) and TBTU (0.0159 g, 0.0495 mmol) in DCM (1 mL) were added to DIEA (0.0287 mL, 0.165 mmol) and stirred at room temperature for 1 hour. The mixture was directly loaded to column and purified by chromatography (1:1 hexane:ethyl acetate) to give (S)-tert-butyl 5-((S)-1-(4-bromophenyl)-2-oxo-2-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyri din-4-yl)piperazin-1-yl)ethyl)-2,2-dimethylpyrrolidine-1-carboxylate as a solid. The solid was dissolved in DCM (1 mL), and TFA (0.2 mL) was added. The mixture was stirred at room temperature for 1 hour. The solvent was removed. The residue was dissolved in DCM (0.5 mL) and 2M HCl in ether (1 mL) was added. The resulting solid was collected by filtration to give (S)-2-(4-bromophenyl)-2-((S)-5,5-dimethylpyrrolidin-2-yl)-1-(4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)ethanone dihydrochloride (0.025 g, 95%). MS APCI (+) m/z 574 detected.

Workup

  1. custompurified by chromatography (1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-5e271669dcef40a7b16bba1d94bdd04c
Source dataset
uspto-grants-2014_09
Patent number
US08841304B2

Reaction notes

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