1-(Prop-2-yn-1-yl)piperidine → HCID 67347544, compound

HRID 1676253Notes

Reaction equation

HRID 1676253 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[F:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][C:17]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]2[CH:25]=[C:26](I)[S:27][C:20]=12)[NH2:14]>>[F:10][C:11]1[CH:12]=[C:13]([NH2:14])[CH:15]=[CH:16][C:17]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]2[CH:25]=[C:26]([C:3]#[C:2][CH2:1][N:4]3[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]3)[S:27][C:20]=12

Participants

3

Reactant 2

HCID 3366521-(Prop-2-yn-1-yl)piperidineHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 67347544HCID 67347544, compoundYield 82.7%

Conditions

Temperature
50 °C

Procedure

Prepared from 1-(prop-2-ynyl)piperidine (24 mg, 0.19 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 5 hours. The crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CHCl3]. The product was obtained as a waxy solid (41 mg, 71%). 1H NMR (400 MHz, CDCl3) δ 8.47 (d, J=6 Hz, 1H), 7.58 (s, 1H), 7.03 (t, J=9 Hz, 1H), 6.52 (m, 3H), 3.85 (br s, 2H), 3.56 (s, 2H), 2.60 (m, 4H), 1.66 (m, 4H), 1.47 (m, 2H).

Workup

  1. customThe crude was purified by preparative TLC [5% MeOH (containing 7N NH3) in CHCl3]

Sources & evidence

ORD record
ord-500d24f40b6547958be1d6cc4bc5f8c2
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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