Cyanamide → US10273222, Example 64

HRID 2277507

반응식

HRID 2277507 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 90406906US10273222, Example 64수율 61.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-fe5d0e53aeab43498569d0221bf695f5
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133166B2

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