Cyanamide → US10273222, Example 64

참여 물질

역할	이름	HCID	투입량
반응물	Cyanamide	HCID 9864	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	US10273222, Example 59	HCID 90407463	—
용매	Dimethylformamide	HCID 6228	—
생성물	US10273222, Example 64	HCID 90406906	61.7%

반응 단계

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.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09133166B2
출처 데이터셋	uspto-grants-2015_09
ORD ID	ord-fe5d0e53aeab43498569d0221bf695f5
출처 메모	uspto-grants-2015_09