Cyanamide → US10273222, Example 64

HRID 2277507ノート

反応式

HRID 2277507 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 90406906US10273222, Example 64収率 61.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-fe5d0e53aeab43498569d0221bf695f5
出典データセット
uspto-grants-2015_09
特許番号
US09133166B2

反応ノート

読み込み中…