HCID 46873758, compound → HCID 46873512, compound

HRID 2272821Notes

Reaction equation

HRID 2272821 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:33])[NH:12][C:13]2[C:14](=[O:32])[O:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([O:23][CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[C:17]=3[CH3:31])=[CH:7][C:6]=1[CH2:34][CH:35]=[C:36]([CH3:38])[CH3:37])(=O)C>C(N(CC)CC)C.CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([NH:12][C:13]2[C:14](=[O:32])[O:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([O:23][CH:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)[C:17]=3[CH3:31])=[O:33])=[CH:7][C:6]=1[CH2:34][CH:35]=[C:36]([CH3:38])[CH3:37]

Participants

3

Reactant 1

HCID 46873758HCID 46873758, compound

Product 1

HCID 46873512HCID 46873512, compound

Reagents, catalysts & solvents 1

HCID 22728368Triethylamine methanolSolvent

Procedure

General procedure IV for the preparation of compounds 31a-g: Compound 29a (52 mg, 0.1 mmol) was dissolved in 10% triethylamine/methanol (3 mL). The solution was stirred at room temperature overnight and concentrated. The residue was purified by column chromatography on silica by using methylene chloride and methanol (10:1) to give 31a as a white, amorphous solid (37 mg, 73%). 1H NMR (500 MHz, DMSOd6) δ 9.22 (s, 1H), 8.47 (s, 1H), 7.68˜7.66 (m, 2H), 7.53 (d, J=8.7, 1H), 7.11 (d, J=8.9, 1H), 6.90 (d, J=8.7, 1H), 5.30 (m, 1H), 4.57 (m, 1H), 3.27 (d, J=7.3, 2H), 2.62˜2.54 (m, 2H), 2.34˜2.28 (m, 2H), 2.22 (s, 3H), 2.21 (s, 3H), 1.96˜1.92 (m, 2H), 1.76˜1.72 (m, 2H), 1.71 (s, 3H), 1.69 (s, 3H). 13C NMR (125 MHz, DMSOd6) δ 165.3, 158.8, 158.4, 156.6, 149.5, 131.9, 129.2, 127.8, 127.7, 126.8, 126.0, 124.0, 122.3, 121.3, 114.6, 113.4, 112.7, 110.8, 72.1, 51.8, 45.7, 30.2, 27.9, 25.6, 17.7, 8.2. IR (film) νmax 3421, 1703, 1666, 1601, 1528, 1504, 1366, 1248, 1178, 1150, 1094, 1040 cm−1. HRMS (ESI+) m/z Calc for [M+H+] C28H33N2O5 477.2389. found: 477.2397.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-f58ba20dd9354ecfab8eabd89588fc2e
Source dataset
uspto-grants-2015_09
Patent number
US09120774B2

Reaction notes

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