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1,2-Dichloroethane → HCID 67408780, compound

HRID 714738
Notes
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Reaction equation

HRID 714738 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[C:10]([CH2:17][N:18]2[C:22](=[O:23])[N:21]([CH2:24][CH:25]([OH:30])[C:26]([F:29])([F:28])[F:27])[C:20]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)=[N:19]2)[CH:9]=1.C1C=CC2N(O)N=[N:44]C=2C=1.C(Cl)CCl.N>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14]([NH2:44])=[O:16])=[C:10]([CH2:17][N:18]2[C:22](=[O:23])[N:21]([CH2:24][CH:25]([OH:30])[C:26]([F:28])([F:29])[F:27])[C:20]([C:31]3[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=3)=[N:19]2)[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 222Ammonia2×HCID 757711-HydroxybenzotriazoleHCID 53379068HCID 53379068, compound

Product 1

HCID 67408780HCID 67408780, compound

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

43 mg (0.08 mmol) of the compound from Example 132 were initially charged in 1 ml of DMF, and 14 mg (0.10 mmol) of HOBt and 19 mg (0.10 mmol) of EDC were added. After 10 min of stirring at RT, 0.41 ml (0.20 mmol) of ammonia solution (35% strength in water) was added, and the mixture was stirred at RT for 16 h. Under reduced pressure, the reaction solution was then freed of excess ammonia, about 3 ml of water were added and the mixture was extracted three times with in each case 5 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 1:3→1:5). This gave 19 mg (42% of theory) of the target compound.

Workup

  1. stirringthe mixture was stirred at RT for 16 h
  2. additionwere added
  3. extractionthe mixture was extracted three times with in each case 5 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 1:3→1:5)

Sources & evidence

ORD record
ord-2961b6d305ab49b2b363a6ac94a063a9
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187466B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes