3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline → N-(3-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)prop-2-ynyl)-2-(pyrrolidin-1-yl)acetamide

HRID 1676241Notes

Reaction equation

HRID 1676241 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17](I)[S:18][C:11]=12)[NH2:5].[CH2:20]([NH:23][C:24](=[O:31])[CH2:25][N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)[C:21]#[CH:22]>>[NH2:5][C:4]1[CH:6]=[CH:7][C:8]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[CH:16]=[C:17]([C:22]#[C:21][CH2:20][NH:23][C:24](=[O:31])[CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[S:18][C:11]=23)=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 2

HCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)anilineHCID 77174863N-(prop-2-ynyl)-2-(pyrrolidin-1-yl)acetamide

Product 1

HCID 67346972N-(3-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)prop-2-ynyl)-2-(pyrrolidin-1-yl)acetamideYield 65%

Procedure

Prepared from 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)benzenamine (Example 6, Step A; 72 mg, 0.186 mmol) and N-(prop-2-ynyl)-2-(pyrrolidin-1-yl)acetamide (34 mg, 0.205 mmol; prepared according to the method described in WO 04/076412A) according to the procedure described for Example 6, Step B, except the reaction was executed at room temperature for 3 hours. The product was purified by preparative TLC (10% MeOH/CH2Cl2). The product was obtained as a waxy solid (69 mg, 65%). 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J=6 Hz, 1H), 7.60 (s, 1H), 7.52 (br s, 1H), 7.03 (t, J=9 Hz, 1H), 6.54 (m, 2H), 6.48 (m, 1H), 4.39 (d, J=6 Hz, 2H), 3.86 (br s, 2H), 3.28 (s, 2H), 2.69 (m, 4H), 1.85 (m, 4H). LRMS (ESI pos) m/e 425 (M+1).

Workup

  1. customprepared
  2. customThe product was purified by preparative TLC (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-884d713bfb4049a683449eebe3f38230
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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