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Triethylamine → HCID 67273738, compound

HRID 1696752
Notes
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Reaction equation

HRID 1696752 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][C:6]=1[CH3:14].Cl[C:16](OC1C=CC=CC=1)=[O:17].C(N(CC)CC)C.[C:32]([Si:36]([CH3:51])([CH3:50])[O:37][CH2:38][CH2:39][NH:40][C:41]1[CH:46]=[C:45]([S:47][CH3:48])[CH:44]=[C:43]([NH2:49])[N:42]=1)([CH3:35])([CH3:34])[CH3:33]>C(#N)C>[C:32]([Si:36]([CH3:51])([CH3:50])[O:37][CH2:38][CH2:39][NH:40][C:41]1[N:42]=[C:43]([NH:49][C:16]([NH:13][S:10]([C:8]2[S:9][C:5]([CH2:4][CH2:3][O:2][CH3:1])=[C:6]([CH3:14])[CH:7]=2)(=[O:12])=[O:11])=[O:17])[CH:44]=[C:45]([S:47][CH3:48])[CH:46]=1)([CH3:35])([CH3:34])[CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 67273555HCID 67273555, compoundHCID 67274431HCID 67274431, compound

Product 1

HCID 67273738HCID 67273738, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent
2×

Conditions

Temperature
60 °C

Procedure

5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonic acid amide (0.082 g, 0.48 mmol) was dissolved in 2.8 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.075 g, 1.0 eq.) and triethylamine (0.167 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. The above prepared N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methylsulfanyl-pyridine-2,6-diamine (0.150 g, 1.0 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. for 18 h. Cooling, pouring onto crashed ice, twofold extraction with AcOEt, washing with brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=1/1), yielded eventually 0.161 g of the title compound as off-white foam.

Workup

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice, twofold extraction with AcOEt
  5. washwashing with brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-dc30795d521243829173aef86531e5bc
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163778B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes