1-Methyl-4-(prop-2-yn-1-yl)piperazine → 3-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 1676254Notes

Reaction equation

HRID 1676254 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]#[CH:10])[CH2:4][CH2:3]1.[F:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27](I)[S:28][C:21]=12)[NH2:15]>>[F:11][C:12]1[CH:13]=[C:14]([NH2:15])[CH:16]=[CH:17][C:18]=1[O:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]2[CH:26]=[C:27]([C:10]#[C:9][CH2:8][N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[S:28][C:21]=12

Participants

3

Reactant 2

HCID 135140911-Methyl-4-(prop-2-yn-1-yl)piperazineHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 673454993-Fluoro-4-(2-(3-(4-methylpiperazin-1-yl)prop-1-ynyl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 77.6%

Conditions

Temperature
50 °C

Procedure

Prepared from 1-methyl-4-(prop-2-ynyl)piperazine (26.8 mg, 0.194 mmol) and 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 50 mg, 0.13 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 eluting with 5% MeOH (containing 7N NH3) in CH2Cl2. The product was obtained as a waxy solid (40 mg, 75%). 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=6 Hz, 1H), 7.58 (s, 1H), 7.03 (m, 1H), 6.53 (m, 3H), 3.86 (br s, 2H), 3.61 (s, 2H), 2.5-2.8 (m, 8H), 2.37 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-e9a12777d0fe4367af9c9d6021f2d0be
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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