Diisopropylethylamine → HCID 59354988, compound

HRID 2196427Notes

Reaction equation

HRID 2196427 reaction equation
CCN(C(C)C)C(C)C.[CH3:10][N:11]1[C:15]([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)=[N:14][CH:13]=[N:12]1.[NH2:25][C@@H:26]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([F:49])([F:48])[F:47])[CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[O:37]=[C:36]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:38])[N:28]1[CH2:27][C@@H:26]([NH:25][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16]([C:15]2[N:11]([CH3:10])[N:12]=[CH:13][N:14]=2)=[CH:24][CH:23]=1)[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([F:48])([F:47])[F:49]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 578268082-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dioneHCID 59355024HCID 59355024, compound

Product 1

HCID 59354988HCID 59354988, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hunig's base (0.084 ml, 0.48 mmol) was added to a suspension of 4-(1-methyl-1H-1,2,4-triazol-5-yl)benzoic acid (39.3 mg, 0.19 mmol), 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione (62 mg, 0.16 mmol), and PyBroP (75 mg, 0.16 mmol) in DCM (1 ml). The reaction mixture became clear and was stirred at RT overnight. The reaction mixture was loaded directly on a 25S Biotage column, which was eluted with 50-100% EA/DCM to give 67.3 mg of product. LC-MS (ES) m/z=534 (M+H)+.

Workup

  1. washwas eluted with 50-100% EA/DCM

Sources & evidence

ORD record
ord-535b7e46c0824455a25230701320f33f
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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