Trifluoroacetic acid → HCID 178428201, compound

HRID 1711269Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([C:17]2[N:18](COCC[Si](C)(C)C)[CH:19]=[C:20]([C:22]#[N:23])[N:21]=2)=[O:16])[CH2:4][CH2:3]1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl.CCO>[F:35][C:34]([F:37])([F:36])[C:32]([OH:38])=[O:33].[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][C:15]([C:17]2[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=2)=[O:16])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 153 mg (0.348 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (5 mL) was treated with EtOH (1 drop) and TFA (1 mL), and the mixture was warmed to 40° C. for 2 h and left at RT for 2 days. The mixture was concentrated to dryness, taken up in CH2Cl2 (5 mL), and treated with EtOH (1 drop) and TFA (1.00 mL) at RT for 7 h. The mixture was concentrated in vacuo. The residue was taken up in MeOH (2.5 mL) and a 10% solution of acetonitrile in water (7.5 mL) to form a suspension. The solid was filtered and triturated with a minimum amount of acetone to afford 50.7 mg (34%) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.35-8.32 (m, 1H), 8.03 (s, 1H), 7.29-7.26 (m, 1H), 7.15-7.12 (m, 2H), 3.09-2.99 (m, 2H), 2.81-2.74 (m, 2H), 1.85-1.80 (m, 2H), 1.72-1.56 (m, 3H), 1.09 (d, 3H, J=6.0 Hz). Mass spectrum (ESI, m/z): Calcd. for C17H19N5O, 310.2 (M+H), found 310.0.

Workup

concentrationThe mixture was concentrated to dryness
additiontreated with EtOH (1 drop) and TFA (1.00 mL) at RT for 7 h
concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-ffb4556b3a8844b8bf09350f56166015
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07790724B2

Reaction notes

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