Trifluoroacetic acid → HCID 86615981, compound

HRID 1190177Notes

Reaction equation

[CH3:1][C:2]1([CH3:28])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([OH:17])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[NH:18][C:19]([C:21]2[NH:22][CH:23]=[C:24]([C:26]#[N:27])[N:25]=2)=[O:20])=[CH:4][CH2:3]1.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32]O.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][O:17][C:14]([C:12]1[CH:11]=[CH:10][C:9]([NH:18][C:19]([C:21]2[NH:25][C:24]([C:26]#[N:27])=[CH:23][N:22]=2)=[O:20])=[C:8]([C:5]2[CH2:6][CH2:7][C:2]([CH3:28])([CH3:1])[CH2:3][CH:4]=2)[CH:13]=1)([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 5-cyano-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(1-hydroxy-1-methyl-ethyl)-phenyl]-amide (60 mg, 0.16 mmol)(as prepared in Example 14, step (d)) in 1 mL of DCM was added 2-dimethylamino-ethanol (0.32 mL, 3.20 mmol), TFA (0.37 mL, 4.80 mmol), and the mixture heated to 60° C. for 6 h. The mixture was concentrated and the title compound purified by RP-HPLC on a C18 column eluting with a linear gradient of 30-55% CH3CN in 0.1% TFA/H2O over 9 min to give 10 mg (11%) of a white solid. 1H-NMR (400 MHz, CD3OD): δ 8.26 (d, J=8.5 Hz, 1H), 8.09 (s, 1H), 7.44 (dd, J=8.5, 2.2 Hz, 1H), 7.30 (d, J=2.2 Hz, 1H), 5.77 (m, 1H), 3.52 (m, 2H), 3.30 (m, 2H), 2.91 (s, 6H), 2.34 (m, 2H), 2.11 (m, 2H), 1.64 (s, 6H), 1.60 (m, 2H), 1.12 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C26H35N5O2, 450.3 (M+H). found 450.0.

Workup

concentrationThe mixture was concentrated
customthe title compound purified by RP-HPLC on a C18 column
washeluting with a linear gradient of 30-55% CH3CN in 0.1% TFA/H2O over 9 min

Sources & evidence

ORD record: ord-41fb787fbee141b693725b4b7ce8fe98
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674100B2

Reaction notes

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