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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-Butyl 2-(methoxy(methyl)carbamoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388676
Notes
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Reaction equation

HRID 2388676 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([OH:19])=O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][O:23][CH3:24].C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:24][O:23][N:22]([CH3:21])[C:17]([C:15]1[S:14][C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][C:10]=2[CH:16]=1)=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 177503995-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid

Product 1

HCID 86635664
Tert-Butyl 2-(methoxy(methyl)carbamoyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid (968 mg, 3.42 mmol) and N,O-dimethylhydroxylamine hydrochloride (333 mg, 3.42 mmol) were dissolved in MC (50 ml) and the solution was cooled to 0° C. HOAt (46.5 mg, 0.34 mmol), diisopropylethylamine (0.66 ml, 3.76 mmol) and EDCI (720 mg, 3.76 mmol) were added to this mixture and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with methylene chloride (50 ml) and washed with 0.5 M KHSO4 solution (100 ml), NaHCO3 solution and NaCl solution. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. The product obtained in this way (1.13 g) was employed in the next stage without further purification.

Workup

  1. washwashed with 0.5 M KHSO4 solution (100 ml), NaHCO3 solution and NaCl solution
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product obtained in this way (1.13 g)
  6. customwas employed in the next stage without further purification

Sources & evidence

ORD record
ord-b24125ca02d24f48ad4bc9b3f6a12269
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08268814B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes