Diisopropylethylamine → HCID 67411574, compound

HRID 909243Notes

Reaction equation

[Si:1]([O:8][C:9]([CH3:31])([CH3:30])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][C:21]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=3[CH2:23][NH2:24])=[CH:17][CH:18]=2)[CH:13]=[N:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC(Cl)(Cl)C[O:35][C:36](=O)[NH:37][C:38]1[N:39]([CH3:47])[N:40]=[C:41]([C:43]([CH3:46])([CH3:45])[CH3:44])[CH:42]=1.CCN(C(C)C)C(C)C>CC(N(C)C)=O.CCOCC>[Si:1]([O:8][C:9]([CH3:31])([CH3:30])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][C:21]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=3[CH2:23][NH:24][C:36]([NH:37][C:38]3[N:39]([CH3:47])[N:40]=[C:41]([C:43]([CH3:45])([CH3:44])[CH3:46])[CH:42]=3)=[O:35])=[CH:17][CH:18]=2)[CH:13]=[N:12]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-{1-[2-(tert-butyldimethylsilanyloxy)-2-methyl-propyl]-1H-indazol-5-yloxy}-5-fluorobenzylamine (0.072 g, 0.162 mmol), (5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloroethyl ester (0.080 g, 0.24 mmol) and DIEA (0.06 mL, 0.324 mmol) in DMA (3 mL) was heated to 80° C. for 16 hours. The mixture was diluted with ether (60 mL) and washed with water (3×5 mL), brine, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed on silica eluting with ethyl acetate/hexanes (3:1) to afford 0.084 g of product (83% yield).

Workup

washwashed with water (3×5 mL), brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was chromatographed on silica eluting with ethyl acetate/hexanes (3:1)

Sources & evidence

ORD record: ord-02fe087516aa42c7ae92acda17139b26
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017641B2

Reaction notes

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