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2-Methoxyethylamine → 1-(4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)-3-(2-methoxyethylamino)propan-1-one

HRID 1942782
Notes
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Reaction equation

HRID 1942782 reaction equation
[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:23])[CH:21]=[CH2:22])[CH2:16][CH:15]=3)[S:13][C:6]=12.[CH3:31][O:32][CH2:33][CH2:34][NH2:35]>C1COCC1.C(Cl)Cl>[F:1][C:2]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH2:19][CH2:18][N:17]([C:20](=[O:23])[CH2:21][CH2:22][NH:35][CH2:34][CH2:33][O:32][CH3:31])[CH2:16][CH:15]=3)[S:13][C:6]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 579196171-(4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one

Product 1

HCID 579196221-(4-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)-3-(2-methoxyethylamino)propan-1-oneYield 45%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of the compound 98 (171.0 mg, 0.4 mmol) and 2-methoxyethanamine (0.14 mL, 1.62 mmol) in THF (98.1 mL) was stirred overnight at room temperature. It was then diluted with DCM, washed with aqueous sodium bicarbonate and water. The organic phase was extracted with 1N HCl, the aqueous acidic phase was basified by addition of 1N NaOH (pH˜11) and extracted with DCM. The DCM extract was dried over anhydrous sodium sulphate and concentrated under reduced pressure affording title compound 99 (89.0 mg, 45% yield) as cream foam. MS (m/z): 501.2 (M+1).

Workup

  1. washwashed with aqueous sodium bicarbonate and water
  2. extractionThe organic phase was extracted with 1N HCl
  3. additionthe aqueous acidic phase was basified by addition of 1N NaOH (pH˜11)
  4. extractionextracted with DCM
  5. extractionThe DCM extract
  6. dry with materialwas dried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-904a7ee4b9fa4a578a8fbdb686be49de
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08389541B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes