Triethylamine → HCID 66614271, compound

HRID 510119Notes

Reaction equation

HRID 510119 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH:21][CH:22]([CH3:24])[CH3:23])=[C:16]([NH2:25])[N:15]=2)=[N:6]1.C1N=CN([C:35](N2C=NC=C2)=[O:36])C=1.C(N(CC)CC)C>CN(C)C=O.O.C(OCC)(=O)C>[NH2:20][C:18]1[N:19]=[C:14]([C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:5]([CH2:4][C:3]3[CH:26]=[CH:27][CH:28]=[CH:29][C:2]=3[F:1])[N:6]=2)[N:15]=[C:16]2[C:17]=1[N:21]([CH:22]([CH3:24])[CH3:23])[C:35](=[O:36])[NH:25]2

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 66613757HCID 66613757, compound

Product 1

HCID 66614271HCID 66614271, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

520 mg (1.33 mmol) of the compound from example 61A were initially charged in dimethylformamide (5 ml), then 1.07 g (6.63 mmol) of N,N-carbonyldiimidazole and 2.31 ml (1.68 mmol) of triethylamine were added and the mixture was stirred at 100° C. overnight. The reaction mixture was then diluted with water and ethyl acetate, the phases were separated and the aqueous phase was extracted with ethyl acetate. The collected organic phases were dried over sodium sulfate, filtered and concentrated. The crude product (540 mg, 84% purity) was not purified any further.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe collected organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product (540 mg, 84% purity) was not purified any further

Sources & evidence

ORD record
ord-608dcb910d9548eb926cfe1a70a860a6
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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