Triethylamine → N-[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonamide

HRID 639081Notes

Reaction equation

HRID 639081 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][C@H:16]([CH2:19][NH2:20])[CH2:15]1)=[N:9][C:8]([O:21][CH3:22])=[CH:7][CH:6]=2.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>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][C@H:16]([CH2:19][NH:20][S:41]([C:38]3[CH:39]=[CH:40][C:34]4[S:33][CH2:32][C:31](=[O:30])[NH:36][C:35]=4[CH:37]=3)(=[O:43])=[O:42])[CH2:15]1)=[N:9][C:8]([O:21][CH3:22])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218737563-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonyl chlorideHCID 68576177[((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amine

Product 1

HCID 11720712N-[((3S)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonamideYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [((3R)-1-{2-[3-fluoro-6-(methyloxy)-1,5-naphthyridin-4-yl]ethyl}-3-pyrrolidinyl)methyl]amine (0.50 g, 1.65 mmole) in dry CH2Cl2 (25 mL) at RT was added triethylamine (0.34 mL, 2.48 mmole) and 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-sulfonyl chloride (0.47 g, 1.80 mmole). After 24 h, the reaction solution was concentrated under vacuum. Purification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH) afforded the title compound (0.80 g, 91%) as light yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.59 (s, 1H), 8.16 (d, J=9.0 Hz, 1H), 7.34 (m, 3H), 7.03 (d, J=9.0 Hz, 1H), 4.04 (s, 3H), 3.47 (s, 2H), 3.34 (m, 2H), 2.95 (m, 3H), 2.79 (m, 2H), 2.61 (m, 1H), 2.52 (m, 2H), 2.34 (m, 1H), 1.97 (m, 1H), 1.55 (m, 1H). LC-MS (ES) m/e 532 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated under vacuum
  2. customPurification on silica (CHCl3/MeOH, 9:1 containing 5% NH4OH)

Sources & evidence

ORD record
ord-35c718dcaaf6429da901f8d9998bb807
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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