Diisopropylethylamine → HCID 178461163, compound

HRID 1510156Notes

Reaction equation

[CH:1]1([NH:7][C:8]2[C@:12]3([CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[CH2:13]3)[N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[C:10](=[O:26])[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:27][C:28]1([CH3:41])[CH:37]=[CH:36][C:35]2[C:30](=[C:31]([C:38](O)=[O:39])[CH:32]=[CH:33][CH:34]=2)[NH:29]1.C(N(C(C)C)CC)(C)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH:1]1([NH:7][C:8]2[C@:12]3([CH2:17][CH2:16][N:15]([C:38]([C:31]4[CH:32]=[CH:33][CH:34]=[C:35]5[C:30]=4[NH:29][C:28]([CH3:41])([CH3:27])[CH:37]=[CH:36]5)=[O:39])[C@@H:14]([CH3:18])[CH2:13]3)[N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)[C:10](=[O:26])[N:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 11-9 (0.309 g, 0.861 mmol) in DMF (10 mL) was added: 2,2-dimethyl-1,2-dihydroquinoline-8-carboxylic acid (0.175 g, 0.861 mmol), diisopropyethylamine (0.334 g, 2.58 mmol) and BOP reagent (0.381 g, 0.861 mmol). After stirring at 50° C. overnight the reaction mixture was diluted with water and extracted using chloroform (three times). The combined organic layer were dried over MgSO4 and concentrated under vacuum. Purification by silica gel chromatography (4% methanol/chloroform/1% triethylamine) afforded the desired product.

Workup

extractionextracted
dry with materialThe combined organic layer were dried over MgSO4
concentrationconcentrated under vacuum
customPurification by silica gel chromatography (4% methanol/chloroform/1% triethylamine)

Sources & evidence

ORD record: ord-c29ace8fd7bf4b879683dc88b792f8ed
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211904B2

Reaction notes

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