(2-Methoxy-phenyl)-acetyl isothiocyanate → N-(3-Fluoro-4-(2-(3-methoxyphenylamino)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(2-methoxyphenyl)acetamide

HRID 1711115Notes

Reaction equation

HRID 1711115 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=4)[S:15][C:8]=23)=[C:4]([F:27])[CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH2:36][C:37]([N:39]=[C:40]=[S:41])=[O:38]>CCO.C1(C)C=CC=CC=1>[F:27][C:4]1[CH:3]=[C:2]([NH:1][C:40]([NH:39][C:37](=[O:38])[CH2:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[O:29][CH3:28])=[S:41])[CH:26]=[CH:25][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)[S:15][C:8]=12

Participants

4

Reactant 2

HCID 21890860(2-Methoxy-phenyl)-acetyl isothiocyanateHCID 594577377-(4-amino-2-fluorophenoxy)-N-(3-methoxyphenyl)thieno[3,2-b]pyridin-2-amine

Product 1

HCID 16717919N-(3-Fluoro-4-(2-(3-methoxyphenylamino)thieno[3,2-b]pyridin-7-yloxy)phenylcarbamothioyl)-2-(2-methoxyphenyl)acetamideYield 25.5%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A solution of 449 (40 mg, 0.10 mmol) in 1:1 mixture of EtOH/toluene (2 mL) was treated with 2-(2-methoxyphenyl)acetyl isothiocyanate (394 mg, 2.22 mmol) and stirred at room temperature for 2 hours. The reaction mixture was then concentrated and purified by flash chromatography using the gradient 75-100% EtOAc in hexanes as an eluent, yielding 447 (15 mg, 24% yield). CDCl3 12.39 (s, 1H), 9.47 (s, 1H), 8.34 (d, J=5.7 Hz, 1H), 7.92 (dd, J=2.0, 11.8 Hz, 1H), 7.36 (m, 2H), 7.22 (m, 2H), 7.01 (m, 3H), 6.80 (s, 2H), 6.59 (d, J=7.4 Hz, 2H), 6.39 (d, J=5.6 Hz, 1H), 4.00 (s, 3H), 3.80 (s, 3H), 3.72 (s, 2H) LCMS: (M+H) 589.0

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-917035ebf362418b818e1bbad23e24f6
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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