Formaldehyde → HCID 11212985, Verbindung

HRID 1987247Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987247
N[C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[C:6]([NH:8][S:9]([C:12]2[C:17]3=[N:18][S:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1.[CH2:29]=O.[C:31]([BH3-])#[N:32].[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C.C(#N)C.C(Cl)Cl>[CH3:29][N:32]([CH3:31])[C:2]1[CH:3]=[CH:4][C:5]([C:21]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])=[C:6]([NH:8][S:9]([C:12]2[C:17]3=[N:18][S:19][N:20]=[C:16]3[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:7]=1

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 11292979HCID 11292979, Verbindung

Produkt 1

HCID 11212985HCID 11212985, VerbindungAusbeute 27,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 21877088Acetonitrile methylene chlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-amino-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 24; 30 mg, 0.072 mmol) in 2:1 acetonitrile/DCM (6 mL), was added formaldehyde (0.1 mL, 3.6 mmol), sodium cyanoborohydride (68 mg, 1.08 mmol) and acetic acid (12 μL). The reaction mixture was stirred for 3 h at room temperature. 1 M NaOH was added until the solution became basic. The mixture was taken up in DCM (5 mL), and washed with water and brine. The organic layer was removed, dried, and purified by preparative reversed-phase HPLC (acetonitrile/water, 0.05% TFA) to afford the title compound (8 mg, 0.02 mmol, 25%). MS (ESI): m/z 446 [M+H]+, 468 [M+Na]+. HPLC (reversed-phase): RT=9.14 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.61 (s, 1H), 8.22 (dd, J=7.0 Hz, 1.0 Hz, 1H), 8.18 (dd, J=8.8 Hz, 1.0 Hz, 1H), 7.63 (dd, J=8.8 Hz, 7.0 Hz, 1H), 6.95 (d, J=2.5 Hz, 7 Hz, 1H), 6.90 (d, J=8.7 Hz, 1H), 6.26 (dd, 8.7 Hz, 2.5 Hz, 1H), 3.16 (s, 4H), 2.95 (s, 6H), 1.56 (m, 2H), 1.42 (m, 4H).

Aufarbeitung

  1. washwashed with water and brine
  2. customThe organic layer was removed
  3. customdried
  4. custompurified by preparative reversed-phase HPLC (acetonitrile/water, 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-00830f6cedba45b696959c4550a7fd5f
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550492B2

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