Trifluoroacetic acid → HCID 178493836, compound

HRID 536215Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:14]([CH2:22][CH2:23][N:24]=3)[C:15]([NH2:21])=[N:16][C:17]=2[C:18]=1[O:19][CH3:20])C1C=CC=CC=1.[C:25]([OH:31])([C:27]([F:30])([F:29])[F:28])=[O:26]>CO>[F:28][C:27]([F:30])([F:29])[C:25]([OH:31])=[O:26].[F:28][C:27]([F:30])([F:29])[C:25]([OH:31])=[O:26].[NH2:21][C:15]1[N:14]2[CH2:22][CH2:23][N:24]=[C:13]2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[C:18]([O:19][CH3:20])[C:17]=2[N:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(Benzyloxy)-6-(4,5-dihydro-1H-imidazol-2-yl)-2-methoxyaniline (Step 7, 30 g, 93 mmol) was added portionwise over 1 h to a round bottom flask containing TFA (400 mL) precooled with an ice bath. The reaction mixture was heated to 60° C. and allowed to stir at this temperature for 17 h at which time it was cooled to rt and the reaction mixture concentrated under reduced pressure. The resulting residue was taken up in DCM and hexanes and concentrated under reduced pressure. The material thus obtained was dissolved in MeOH and DCM (250 mL, 1:1) and concentrated under reduced pressure. The resulting solid was dried overnight under vacuum with low heat to give the title compound (100%): 1H NMR (DMSO-d6) δ: 7.61 (1H, m), 6.87 (1H, m), 4.15 (2H, br t), 4.00 (2H, m), 3.64 (3H, s).

Workup

customprecooled with an ice bath
temperaturewas cooled to rt
concentrationthe reaction mixture concentrated under reduced pressure
concentrationhexanes and concentrated under reduced pressure
customThe material thus obtained
concentrationDCM (250 mL, 1:1) and concentrated under reduced pressure
customThe resulting solid was dried overnight under vacuum
temperaturewith low heat

Sources & evidence

ORD record: ord-95b3caaf46d14070b18d160e80b9664e
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859572B2

Reaction notes

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