HCID 68244627, compound → HCID 118108312, compound

HRID 2174519Notes

Reaction equation

HRID 2174519 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH3:15])=[CH:9]2)[CH2:2][CH2:3][CH3:4].CC1NC2C(C=1[CH:26]=[O:27])=CC(OCCC)=CC=2>>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH3:15])=[C:9]2[CH:26]=[O:27])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 68244627HCID 68244627, compoundHCID 100304374HCID 100304374, compound

Product 1

HCID 118108312HCID 118108312, compoundYield 94%

Procedure

This compound was prepared from 408d (300 mg, 1.48 mmol) in a manner similar to that for 409b to yield a cream-colored powder (320 mg, 94%): mp 160-161° C. TLC Rf 0.45 (3:1 EtOAc/hexanes). 1H NMR (600 MHz, d6-DMSO) δ 11.85 (s, 1H), 10.00 (s, 1H), 7.55 (d, 1H, J=2.46 Hz), 7.26-7.25 (d, 1H, J=8.7 Hz), 6.79-6.77 (dd, 1H, J1=8.7 Hz, J2=2.46 Hz), 3.96-3.94 (t, 2H, J=6.48 Hz), 2.64 (s, 3H), 1.73-1.68 (quin, 2H, J=6.48 Hz), 1.49-1.42 (sex, 2H, J=7.38 Hz), 0.95-0.93 (t, 3H, J=7.38 Hz). 13C NMR (150 MHz, d6-DMSO) δ 185.0, 154.9, 148.5, 130.0, 126.4, 113.6, 112.26, 112.04, 103.2, 67.4, 31.0, 18.8, 13.8, 11.5. Elemental analysis calculated for C14H17NO2: C, 72.70; H, 7.41; N, 6.06. Found: C, 72.87; H, 7.47; N, 6.13.

Sources & evidence

ORD record
ord-2059d84ec3d24e79ac0e0f583352df72
Source dataset
uspto-grants-2015_06
Patent number
US09061994B1

Reaction notes

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