Trifluoroacetic acid → HCID 21873402, compound

HRID 723354Notes

Reaction equation

[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[C:13]1([CH3:27])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1.CO[CH:30](OC)[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][N:42]([CH3:44])[CH3:43])=[CH:35][CH:34]=1.FC(F)(F)C(O)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:44][N:42]([CH3:43])[CH2:41][CH2:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([N:32]2[CH:31]=[CH:30][N:26]([C:23]3[CH:22]=[CH:21][C:20]([O:19][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[CH3:27])=[CH:25][CH:24]=3)[C:1]2=[O:2])=[CH:38][CH:37]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Carbonyldiimidazole (40 mg) was added to a solution of 4-o-tolyloxyphenylamine (50 mg) in dimethylformamide (2 mL) at 0° C. After 30 minutes, (2,2-dimethoxyethyl)-[4-(2-dimethylaminoethoxy)phenyl]amine (67 mg) was added, and the mixture was heated at 80° C. for 2 hours. After cooling to room temperature, trifluoroacetic acid (0.5 mL) was added and the mixture was left to stand for 72 hours. The reaction solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. The organic phase was dried and concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 429.52 (C26H27N3O3); MS (ESI): 430 ([M+H]+), was obtained as hydrotrifluoroacetate in this way.

Workup

temperatureAfter cooling to room temperature
waitthe mixture was left
waitto stand for 72 hours
washwashed with saturated sodium bicarbonate solution
customThe organic phase was dried
concentrationconcentrated
customThe residue was purified by preparative HPLC
customMS (ESI): 430 ([M+H]+), was obtained as hydrotrifluoroacetate in this way

Sources & evidence

ORD record: ord-a46f2375f0a44419bf14d3bde4c87df0
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141561B2

Reaction notes

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