HCID 55285521, compound → HCID 59749717, compound

HRID 747652Notes

Reaction equation

[NH2:1][C:2]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:18]([C:20]1[CH:35]=[CH:34][C:23]([C:24]([NH:26][CH2:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[O:25])=[CH:22][CH:21]=1)=O.N=[C:37]([CH2:42][CH:43]([CH3:45])[CH3:44])[CH2:38][C:39]([NH2:41])=[O:40]>CCO>[CH2:7]([O:6][C:4]([C:3]1[CH:18]([C:20]2[CH:35]=[CH:34][C:23]([C:24](=[O:25])[NH:26][CH2:27][C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:22][CH:21]=2)[C:38]([C:39](=[O:40])[NH2:41])=[C:37]([CH2:42][CH:43]([CH3:45])[CH3:44])[NH:1][C:2]=1[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=1)=[O:5])[CH3:8]

Participants

Conditions

Temperature: 120 °C

Procedure

Ethyl 3-amino-5-(4-fluorophenyl)-2-pentenoate 4 (119 mg, 0.5 mmol), 4-formyl-N-pyridin-3-ylmethyl-benzamide 8 (120 mg, 0.5 mmol) and 3-Imino-5-methyl-hexanoic acid amide 11 (92 mg, 0.65 mmol) were dissolved in EtOH (4 mL). The reaction was stirred at 120° C. overnight. The crude reaction mixture was purified via reverse phase LC/MS to yield, 29 mg of target material. The compound was characterized by NMR and LC/MS. 1H NMR (500 MHz, CDCl3): δ 8.79 (s, 1H), 8.51 (d, J=4.7 Hz, 1H), 8.29 (d, J=7.9 Hz, 1H), 7.68 (m, 4H), 7.28 (d, J=8.5 Hz, 1H), 7.08 (m, 2H), 6.90 (m, 2H), 4.63 (br. s, 2H), 4.04 (q, J=6.8 Hz, 2H), 3.37 (s, 1H), 2.86 (q, J=7.2 Hz, 2H), 2.78 (m, 3H), 2.50 (m, 1H), 1.65 (m, 1H), 1.17 (t, J=6.7 Hz, 3H), 0.82 (t, J=6.9 Hz, 6H).

Workup

customThe crude reaction mixture
customwas purified via reverse phase LC/MS
customto yield

Sources & evidence

ORD record: ord-36fd75c82774475896d84d44d8744887
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396936B1

Reaction notes

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