Cyanamide → US10273222, Example 64

HRID 2277507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2277507
[CH:1]1([CH2:4][N:5]([CH3:22])[CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]([OH:21])=O)[CH:16]=[CH:15][N:14]=3)[N:10]=[CH:9]2)[CH2:3][CH2:2]1.[N:23]#[C:24][NH2:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:24]([NH:25][C:19]([C:17]1[CH:16]=[CH:15][N:14]=[C:13]([C:11]2[N:10]=[CH:9][N:8]([CH2:7][CH2:6][N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[CH3:22])[CH:12]=2)[CH:18]=1)=[O:21])#[N:23]

Komponenten

5

Edukt 3

HCID 9864CyanamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90407463US10273222, Example 59

Produkt 1

HCID 90406906US10273222, Example 64Ausbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(1-{2-[(cyclopropylmethyl)(methyl)amino]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylic acid (10 mg, 0.03 mmol, Example 59), cyanamide (4 mg, 0.1 mmol), HATU (38 mg, 0.1 mmol), TEA (29 μL, 0.2 mmol) in DMF (2 mL) was stirred at r.t. for 1 hr. The reaction mixture was purified by ISCO flash column chromatography (MeOH/DCM=0-50%) to give the title compound as off-white solid (6 mg, 60%). 1HNMR (400 MHz, DMSO-d6): δ 0.43 (2H, m), 0.79 (2H, m), 1.15 (1H, m), 2.30 (5H, m), 2.76 (2H, m), 4.11 (2H, t, J=4.2 Hz), 7.29 (1H, m), 7.73 (1H, d, J=11.4 Hz), 8.27 (1H, s), 8.29 (1H, s), 8.49 (1H, s). [M+H] Calc'd for C17H20N6O, 325. Found, 325.

Aufarbeitung

  1. customThe reaction mixture was purified by ISCO flash column chromatography (MeOH/DCM=0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-fe5d0e53aeab43498569d0221bf695f5
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133166B2

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