Diisopropylethylamine → HCID 10189716, compound

HRID 490006Notes

Reaction equation

HRID 490006 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][C:12]([C:14]3[C:15]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[CH:9]=2)[N:4]([CH3:30])[C:3]=1[C:31](O)=[O:32].Cl.[CH:35]([NH:38][C:39](=[O:48])[C@H:40]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH2:41])([CH3:37])[CH3:36].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:35]([NH:38][C:39](=[O:48])[CH:40]([NH:41][C:31]([C:3]1[N:4]([CH3:30])[C:5]2[C:10]([C:2]=1[Cl:1])=[CH:9][C:8]([NH:11][C:12]([C:14]1[C:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=3)=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:13])=[CH:7][CH:6]=2)=[O:32])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 22262699HCID 22262699, compoundHCID 45158387HCID 45158387, compound

Product 1

HCID 10189716HCID 10189716, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (e) (292.5 mg, 0.619 mmol), (S)-N-isopropyl-2-phenylglycinamide hydrochloride salt (182.1 mg, 0.797 mmol), PyBroP (415.8 mg, 0.865 mmol) were suspended in anhydrous CH2Cl2 (6 ml), followed by the addition of DIEA (0.36 ml, 2.07 mmol). The reaction mixture was stirred at room temperature for 3.5 h. The product was purified by flash chromatography using 30:70 of hexane:EtOAc to afford 345.5 mg of the title compound.

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-b1d59c83bd9f4032924504cea753761f
Source dataset
uspto-grants-2005_12
Patent number
US06979692B2

Reaction notes

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