1,2-Dichloroethane → HCID 10027778, compound

HRID 1435881Notes

Reaction equation

HRID 1435881 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:15]=[CH:16][C:17]([CH2:20][CH2:21][NH2:22])=[N:18][CH:19]=1.C(N(C(C)C)CC)(C)C.[O:32]=[C:33]1[CH2:38][S:37][C:36]2[CH:39]=[CH:40][C:41]([C:43](O)=[O:44])=[N:42][C:35]=2[NH:34]1.O.OC1C2N=NNC=2C=CC=1.C(Cl)CCl>CN(C=O)C>[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:15]=[CH:16][C:17]([CH2:20][CH2:21][NH:22][C:43]([C:41]2[CH:40]=[CH:39][C:36]3[S:37][CH2:38][C:33](=[O:32])[NH:34][C:35]=3[N:42]=2)=[O:44])=[N:18][CH:19]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 218737873-Oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acidHCID 68441439(2-{5-[6-(Methyloxy)-1,5-naphthyridin-4-yl]-2-pyridinyl}ethyl)amine hydrochloride saltHCID 178526939HCID 178526939, compound

Product 1

HCID 10027778HCID 10027778, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (2-{5-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-pyridinyl}ethyl)amine hydrochloride salt (1.08 mmole) in DMF (25 mL) at RT was added diisopropylethylamine (0.75 mL, 4.32 mmole), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (0.23 g, 1.08 mmole), hydroxybenzotriazole hydrate (0.16 g, 1.19 mmole) and EDC (0.23 g, 1.19 mmole). After 18 h, the reaction contents were concentrated and dried under high vacuum. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.40 g, 79%) as light yellow solid: 1H NMR (400 MHz, CD3OD) δ 9.55 (m, 1H), 9.19 (m, 1H), 9.09 (d, J=8.3 Hz, 1H), 8.53 (d, J=9.2 Hz, 1H), 8.42 (m, 1H), 8.23 (d, J=7.7 Hz, 1H), 7.88 (d, J=8.3 Hz, 1H), 7.61 (m, 2H), 4.5 (s, 3H), 4.02 (m, 2H), 3.62 (m, 2H), 3.54 (m, 2H). LC-MS (ES) m/e 473 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-96fcc2335d0840368e1057df58180080
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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