Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate → N-cyclobutyl-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxamide

HRID 1713133Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713133
Cl.[CH:2]1([NH:6][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][N:14]([CH2:19][C:20]([OH:22])=O)[CH2:13][CH2:12][C:11]=3[N:10]=2)=[O:8])[CH2:5][CH2:4][CH2:3]1.[CH:23]1([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][CH2:25][CH2:24]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>C(Cl)Cl>[CH:2]1([NH:6][C:7]([C:9]2[CH:18]=[CH:17][C:16]3[CH2:15][N:14]([CH2:19][C:20]([N:30]4[CH2:31][CH2:32][N:27]([CH:23]5[CH2:26][CH2:25][CH2:24]5)[CH2:28][CH2:29]4)=[O:22])[CH2:13][CH2:12][C:11]=3[N:10]=2)=[O:8])[CH2:3][CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 47386021-CyclobutylpiperazineHCID 66877729{2-[(cyclobutylamino)carbonyl]-7,8-dihydro-1,6-naphthyridin-6(5H)-yl}acetic acid hydrochloride

Produkt 1

HCID 59463539N-cyclobutyl-6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of {2-[(cyclobutylamino)carbonyl]-7,8-dihydro-1,6-naphthyridin-6(5H)-yl}acetic acid hydrochloride (37 mg, 0.11 mmol), 1-cyclobutylpiperazine (19 mg, 0.133 mmol), BOP (59 mg, 0.133 mmol) and TEA (0.075 ml, 0.532 mmol) in DCM (5 ml) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (10 mL). The layers are separated and the aqueous layer is extracted with EtOAc (10 ml). The combined extracts are washed with brine (10 mL), dried and evaporated. The residue is purified by PTLC to give the title compound as a light yellow oil. MS (M+1): 412.4; 1H NMR (δ, CDCl3): 8.11 (d, 1H), 7.94 (d, 1H), 7.43 (d, 1H), 4.53-4.61 (m, 1H), 3.75 (s, 2H), 3.58-3.66 (m, 4H), 3.45 (t, 2H), 3.40 (s, 2H), 3.04 (t, 2H), 2.92 (t, 2H), 2.63-2.76 (m, 1H), 2.36-2.46 (m, 2H), 2.25-2.32 (m, 6H), 1.63-2.06 (m, 6H).

Aufarbeitung

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (10 mL) and EtOAc (10 mL)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (10 ml)
  5. washThe combined extracts are washed with brine (10 mL)
  6. customdried
  7. customevaporated
  8. customThe residue is purified by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-2dc04d11e7f94256ac76cb3ec97dd594
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795262B2

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