HCID 11164883, compound → HCID 11209581, compound

HRID 606637Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:33])[C:11]([C:31]#[N: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(Br)=C(CC3C4C(=CC=CC=4)C=CC=3)C(C3C=CC=CC=3)=C2SC1)=O.COC([C@H]1N2C(=O)C(Br)=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]([C:31]#[N: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 11164883HCID 11164883, compound

HCID 11339937HCID 11339937, compound

HCID 11785440HCID 11785440, compound

Product 1

HCID 11209581HCID 11209581, compoundYield 86%

Procedure

By following the procedure described for the preparation of 6a from 5a, 5c (150 mg, 0.39 mmol) gave 6c as a pale yellow foam (110 mg, 86%): [α]D-161 (c 1.0, CHCl3); IR λ 3012, 2956, 2215, 1749, 1648, 1440, 1365, 1257,1216 cm−1. 1H NMR (400 MHz, CDCl3) δ7.50-7.39 (m, 3H), 7.25-7.18 (m, 2H), 5.72 (dd, J=8.8, 2.3, 1H), 3.85 (s, 3H), 3.72 (dd, J=11.9, 8.8, 1H), 3.51 (dd, J=11.9, 2.3, 1H), 2.21 (s, 3H); 13C NMR (100 MHz, CDCl3) δ167.6, 158.8, 158.4, 154.3, 135.0, 129.7, 129.5, 129.1 (splitted), 128.9, 116.5, 115.4, 99.5, 64.1, 53.5, 31.7, 20.0; HRMS (FAB+) calcd for C17H15N2O3S 327.0803, obsd 327.0805.

Sources & evidence

ORD record: ord-e5d485026b1f4414b01545c27d5fb9f9
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07915417B2

Reaction notes

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