Triethylamine → 3-Oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-sulfonic acid {2-[4-(6-methoxy-[1,5]naphthyridin-4-yl)phenyl]ethyl}amide

HRID 1435873Notes

Reaction equation

HRID 1435873 reaction equation
Cl.[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.[O:30]=[C:31]1[NH:36][C:35]2[CH:37]=[C:38]([S:41](Cl)(=[O:43])=[O:42])[CH:39]=[CH:40][C:34]=2[S:33][CH2:32]1>C(Cl)Cl>[CH3:2][O:3][C:4]1[N:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[C:7]2[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH:22][S:41]([C:38]2[CH:39]=[CH:40][C:34]3[S:33][CH2:32][C:31](=[O:30])[NH:36][C:35]=3[CH:37]=2)(=[O:43])=[O:42])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218737563-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonyl chlorideHCID 684436432-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamine hydrochloride salt

Product 1

HCID 103914833-Oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-sulfonic acid {2-[4-(6-methoxy-[1,5]naphthyridin-4-yl)phenyl]ethyl}amideYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-[4-(6-Methoxy-[1,5]naphthyridin-4-yl)phenyl]ethylamine hydrochloride salt (0.10 g, 0.26 mmole), from Example 1a, in dry CH2Cl2 (25 mL) at RT was added triethylamine (0.11 mL, 0.78 mmole) and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-sulfonyl chloride (69 mg, 0.26 mmole). After 24 h, the reaction contents were concentrated. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.10 g, 75%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 9.06 (d, J=4.5 Hz, 1H), 8.57 (d, J=9.0 Hz, 1H), 8.26 (d, J=4.6 Hz, 1H), 8.10 (d, J=9.1 Hz, 2H), 7.73 (m, 3H), 7.45 (d, J=9.0, 1H), 7.17 (m, 2H), 4.25 (s, 2H), 4.06 (s, 3H), 3.77 (m, 2H), 3.31 (m, 2H). LC-MS (ES) m/e 507 (M+H)+.

Workup

  1. customthe reaction contents
  2. concentrationwere concentrated
  3. customPurification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-d255e9ceb5764255b7fc06f52ead24eb
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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