1,2-Dichloroethane → HCID 59026129, compound

HRID 639114Notes

Reaction equation

HRID 639114 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][C@@H:17]([CH2:20][NH2:21])[CH2:16]1.C(N(C(C)C)CC)(C)C.[O:31]=[C:32]1[CH2:37][S:36][C:35]2[CH:38]=[CH:39][C:40]([C:42](O)=[O:43])=[N:41][C:34]=2[NH:33]1.O.OC1C2N=NNC=2C=CC=1.C(Cl)CCl>CN(C=O)C>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][C@@H:17]([CH2:20][NH:21][C:42]([C:40]2[CH:39]=[CH:38][C:35]3[S:36][CH2:37][C:32](=[O:31])[NH:33][C:34]=3[N:41]=2)=[O:43])[CH2:16]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 59026168HCID 59026168, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 59026129HCID 59026129, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [((3S)-1-{2-[6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amine (0.14 g, 0.49 mmole) in dry in DMF (25 mL) at RT was added diisopropylethylamine (0.10 mL, 0.54 mmole), 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylic acid (0.10 g, 0.49 mmole), hydroxybenzotriazole hydrate (0.73 g, 0.54 mmole) and EDC (0.10 g, 0.54 mmole). After 18 h, the reaction contents were concentrated under high vacuum. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.17 g, 75%) as a light yellow solid: 1H NMR (400 MHz, CD3OD) δ 9.05 (m, 1H), 8.47 (d, J=9.2 Hz, 1H), 8.25 (m, 2H), 7.92 (m, 1H), 7.72 (m, 1H), 7.62 (d, J=9.2 Hz, 1H), 4.22 (s, 3H), 3.91 (m, 2H), 3.82 (m, 2H), 3.67 (s, 2H), 3.65 (m, 2H), 3.44 (m, 2H), 3.18 (m, 2H), 2.98 (m, 1H), 2.37 (m, 1H), 2.05 (m, 1H). LC-MS (ES) m/e 479 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-afc7a42d631d41a191681e66aca7509e
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

Loading…