HCID 11209581, compound → HCID 11438923, compound

HRID 2218520Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:33])[C:11]([CH2:31][NH2:32])=[C:12]([CH2:20]C3C4C(=CC=CC=4)C=CC=3)[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:8]2[S:7][CH2:6]1)=[O:4].COC([C@H]1N2C(=O)C(C#N)=C(CC3C4C(=CC=CC=4)C=CC=3)C(C3C=CC=CC=3)=C2SC1)=O.COC([C@H]1N2C(=O)C(C#N)=C(C)C(C3C=CC=CC=3)=C2SC1)=O>>[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:33])[C:11]([CH2:31][NH2:32])=[C:12]([CH3:20])[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:8]2[S:7][CH2:6]1)=[O:4]

Participants

Reactant 3

HCID 11209581HCID 11209581, compound

HCID 11213235HCID 11213235, compound

HCID 11339937HCID 11339937, compound

Product 1

HCID 11438923HCID 11438923, compoundYield 67%

Procedure

By following the procedure described for the preparation of 7a from 6a, 6c (36 mg, 0.11 mmol) gave 7c as a yellow solid (27 mg, 67%): [α]D−110 (c 0.13, CHCl3); IR λ 2956, 1747, 1631, 1575, 1490, 1442, 1216 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.49-7+(m, 3H), 7.25-7.15 (m, 2H), 5.64 (dd, J=8.5, 2.4, 1H), 3.92-3.69 (m, 7H), 3.62 (dd, J=11.5, 8.6, 1H), 3.41 (dd, J=11.6, 2.3, 1H), 2.02 (s, 3H); 13C NMR (100 MHz, CDCl3) 6168.8, 161.1, 152.0, 147.8, 136.4, 130.0, 129.9, 129.0, 128.9, 128.5, 118.0, 115.3, 64.0, 53.6, 37.9, 31.7, 18.0; MS (ES+) calcd 331 for C17H20N2O3S, obsd 331.

Sources & evidence

ORD record: ord-0774b18938874b859ad29b30b54f2c98
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07411066B2

Reaction notes

Loading…