HCID 68972648, compound → HCID 68972401, compound

HRID 1929534Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].C([O:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:22][C:23]1[C:24]([CH3:31])=[C:25]([CH3:30])[C:26](=[O:29])[NH:27][NH+:28]=1)=[O:17])[CH3:15])=O)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O.CC#N>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:35][C:34]1[CH:33]=[CH:32][C:21]([CH2:22][C:23]2[C:24]([CH3:31])=[C:25]([CH3:30])[C:26](=[O:29])[NH:27][NH+:28]=2)=[CH:20][C:19]=1[N:18]1[C:16](=[O:17])[CH:14]([CH3:15])[NH:13][C:11]1=[O:10]

Participants

Conditions

Temperature: 180 °C

Procedure

To a solution of O2 in DMF (0.1 M) was added DMAP (3 eq) and the mixture was heated in a microwave oven at 180° C. for 2 h. The product was isolated by purification at prep RP-HPLC using H2O (+0.1% TFA) and MeCN (+0.1% TFA) as eluents. The desired fractions were lyophilized to afford the desired compound. 1H NMR (300 MHz, DMSO-d6) δ: 12.67 (1H, s), 8.52 (1H, s), 7.35-7.28 (2H, m), 7.25-7.18 (1H, m), 4.36-4.26 (1H, m), 3.97 (2H, s), 2.06-1.97 (6H, m), 1.38-1.31 (3H, m). MS (ES) C17H18FN4O3 requires: 344. found: 345 (M+H)+.

Workup

customThe product was isolated by purification at prep RP-HPLC

Sources & evidence

ORD record: ord-5ddb5e214bdd427f9242541bf0756eab
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188084B2

Reaction notes

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