HCID 70369569, compound → HCID 86719497, compound

HRID 1772262Notes

Reaction equation

HRID 1772262 reaction equation
[O:1]=[C:2]([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[C:3]([O:5]CC)=O.[NH2:19][CH2:20][CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH:26]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[C:32]([C:39]([F:42])([F:41])[F:40])[CH:31]=2)[CH2:25][CH2:24]1>O1CCCC1>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]([NH:29][CH:26]2[CH2:25][CH2:24][CH:23]([O:22][CH2:21][CH2:20][NH:19][C:3](=[O:5])[C:2]([NH:8][C:9]3[CH:18]=[CH:17][C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[N:10]=3)=[O:1])[CH2:28][CH2:27]2)=[CH:31][C:32]=1[C:39]([F:40])([F:41])[F:42])([O-:38])=[O:37]

Participants

4

Reactant 2

HCID 70369569HCID 70369569, compoundHCID 86719488HCID 86719488, compound

Product 1

HCID 86719497HCID 86719497, compoundYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of ethyl 2-oxo-2-(quinolin-2-ylamino)acetate (56 mg, 0.23 mmol) and N—(-4-(2-aminoethoxy)cyclohexyl)-4-nitro-3-(trifluoromethyl)benzenamine (80 mg, 0.23 mmol) in tetrahydrofuran (2 mL) was stirred overnight at room temperature and then concentrated under vacuum to give a residue, which was purified by HPLC to afford N1-(2-(-4-(4-nitro-3-(trifluoromethyl)phenylamino) cyclohexyloxy)ethyl)-N2-(quinolin-2-yl)oxalamide as a yellow solid (58.8 mg, 46%). (ES, m/z): [M+H]+ 546.10; 1H NMR (400 MHz, CDCl3): δ 10.11 (br s, 1H), 8.41 (d, J=8.8 Hz, 1H), 8.26 (d, J=8.8 Hz, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.93 (d, J=8.8 Hz, 1H), 7.82 (d, J=7.6 Hz, 2H), 7.73 (t, J=7.2 Hz, 1H), 7.52 (t, J=7.2 Hz, 1H), 6.85 (d, J=2.4 Hz, 1H), 6.65 (dd, J=8.8, 2.4 Hz, 1H), 4.48 (d, J=7.2 Hz, 1H), 3.68-3.58 (m, 4H), 3.42-3.36 (m, 2H), 2.19-2.10 (m, 4H), 1.48-1.38 (m, 2H), 1.34-1.24 (m, 2H).

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a residue, which
  3. customwas purified by HPLC

Sources & evidence

ORD record
ord-d1f3e996ae7a4983b5a197051f2c8eba
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

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