Diisopropylethylamine → 1,2,3,4-Tetrahydro-1,8-naphthyridine

HRID 419068

Reaktionsgleichung

Reaktionsgleichung von HRID 419068
[Cl:1][C:2]1[CH:3]=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:16]=2)(=[O:14])=[O:13])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.[NH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][N:34]=2)[CH2:29][CH2:28][CH2:27]1.[N:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][N:44]=2)[CH:39]=[CH:38][CH:37]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>>[NH:34]1[C:35]2[C:30](=[CH:29][CH:28]=[CH:27][N:26]=2)[CH2:31][CH2:32][CH2:33]1.[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C:4]2[C:5]([C:8]([N:44]3[C:45]4[C:40](=[CH:39][CH:38]=[CH:37][N:36]=4)[CH2:41][CH2:42][CH2:43]3)=[O:9])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)(=[O:13])=[O:14])=[CH:16][C:17]=1[C:22]([F:25])([F:23])[F:24]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 1360691,8-NaphthyridineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 130473671,2,3,4-Tetrahydro-1,8-naphthyridineHCID 579420775-Chloro-3-(4-chloro-3-trifluoromethyl benzenesulfonylamino)-pyridine-2-carboxylic acid

Produkt 2

HCID 130473671,2,3,4-Tetrahydro-1,8-naphthyridineHCID 579423234-chloro-N-[5-chloro-2-(3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide

Versuchsvorschrift

5-Chloro-3-(4-chloro-3-(trifluoromethyl)phenylsulfonamido)picolinic acid (208 mg, 0.50 mmol), 1,2,3,4-tetrahydro-[1,8]naphthyridine [(135 mg, 1.0 mmol) 1,2,3,4-tetrahydro-[1,8]naphthyridine was prepared freshly from 1,8-napthyridine via hydrogenation over Pt2O], BOP (486 mg, 1.1 mmol), DIEA (185 mg, 1.4 mmol) were reacted according to the procedure D to provide the title compound. HPLC purification (20→90% gradient of MeCN-water) provided 4-chloro-N-[5-chloro-2-(3,4-dihydro-2H-[1,8]naphthyridine-1-carbonyl)-pyridin-3-yl]-3-trifluoromethyl-benzenesulfonamide: MS m/z: 531.0 (M+H).

Aufarbeitung

  1. customwere reacted

Quellen und Nachweise

ORD-Eintrag
ord-9696dc3f1b6b40a9912ee1c1b98ad082
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093247B2

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