3-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline → HCID 67348983, compound

HRID 1676257Notes

Reaction equation

HRID 1676257 reaction equation
[CH3:1][N:2]([CH3:12])[CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]#[CH:11])[CH2:5][CH2:4]1.[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[CH:28]=[C:29](I)[S:30][C:23]=12)[NH2:17]>>[NH2:17][C:16]1[CH:18]=[CH:19][C:20]([O:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[CH:28]=[C:29]([C:11]#[C:10][CH2:9][N:6]4[CH2:5][CH2:4][CH:3]([N:2]([CH3:12])[CH3:1])[CH2:8][CH2:7]4)[S:30][C:23]=23)=[C:14]([F:13])[CH:15]=1

Participants

3

Reactant 2

HCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)anilineHCID 60768076HCID 60768076, compound

Product 1

HCID 67348983HCID 67348983, compound

Conditions

Temperature
50 °C

Procedure

Prepared from N,N-dimethyl-1-(prop-2-ynyl)piperidin-4-amine (32 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 7 hours. The crude was partially purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]. The product was obtained as a waxy solid (34 mg, 31%; 50% purity by 1H NMR), and carried forward without further purification. LRMS (APCI pos) m/e 425 (M+1).

Workup

  1. customThe crude was partially purified by preparative TLC [5% MeOH (containing 7N NH3) in CH2Cl2]
  2. customThe product was obtained as a waxy solid (34 mg, 31%; 50% purity by 1H NMR)
  3. customcarried forward without further purification

Sources & evidence

ORD record
ord-e39edb0c2b8546fba0c8c0d07c858e75
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

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