Ethylamine → HCID 59437250, compound

HRID 244417Notes

Reaction equation

[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].[CH2:13](N)[CH3:14].[F:16][C:17]([F:40])([F:39])[C:18]([C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[NH:35][N:34]=[CH:33]2)([C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]([CH3:29])[CH:21]=1)[OH:19]>N1C=CC=CC=1>[CH2:7]([NH:3][C:1]([N:35]1[C:36]2[C:32](=[CH:31][C:30]([C:18]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]([CH2:29][CH:13]=[CH2:14])[CH:21]=3)([OH:19])[C:17]([F:16])([F:39])[F:40])=[CH:38][CH:37]=2)[CH:33]=[N:34]1)=[O:2])[CH3:6]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of carbonyldiimidazole (0.282 mmol) in 1 mL pyridine was added ethylamine (0.282 mmol; 2.0 M in THF) dropwise. The mixture was stirred 5 hours and then 2,2,2-trifluoro-1-(1H-indazol-5-yl)-1-(1-methyl-1H-indol-3-yl)ethanol (0.189 mmol) was added. The mixture was heated at 100° C. for 16 hours in a sealed tube. Removal of the volatiles provided a residue which was purified by flash silica gel chromatography using 33% ethyl acetate in hexanes. The product-rich fractions were concentrated in vacuo to afford the title compound (0.045 mmol), m.p. 162° C.-164° C.

Workup

customRemoval of the volatiles
customprovided a residue which
customwas purified by flash silica gel chromatography
concentrationThe product-rich fractions were concentrated in vacuo

Sources & evidence

ORD record: ord-c049ed2aea564a1cb1a54dfb963b1160
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658637B2

Reaction notes

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