1-Ethyl-4-(prop-2-ynyl)piperazine → HCID 67348454, compound

HRID 1676255Notes

Reaction equation

HRID 1676255 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]#[CH:11])[CH2:5][CH2:4]1)[CH3:2].[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]2[CH:27]=[C:28](I)[S:29][C:22]=12)[NH2:16]>>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]#[C:11][C:28]2[S:29][C:22]3[C:23](=[N:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][C:13]=3[F:12])[CH:27]=2)[CH2:5][CH2:4]1)[CH3:2]

Participants

3

Reactant 2

HCID 211907411-Ethyl-4-(prop-2-ynyl)piperazineHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 67348454HCID 67348454, compoundYield 45%

Conditions

Temperature
50 °C

Procedure

Prepared from 1-ethyl-4-(prop -2-ynyl)piperazine (59 mg, 0.39 mmol) and 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 100 mg, 0.26 mmol) according to the procedure described for Example 6, Step B, except the reaction was heated at 50° C. for 7 hours. The crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]. The product was obtained as a waxy solid (48 mg, 40%). 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=6 Hz, 1H), 7.58 (s, 1H), 7.03 (t, J=9 Hz, 1H), 6.53 (m, 2H), 6.47 (m, 1H), 3.86 (br s, 2H), 3.60 (s, 2H), 2.45-2.74 (m, 8H), 2.46 (q, J=7 Hz, 2H), 1.11 (t, J=7 Hz, 3H).

Workup

  1. customThe crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]

Sources & evidence

ORD record
ord-ff0f4d7d4a98462096b6207988fbec0d
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…