Triethylamine → HCID 86596994, compound

HRID 494728Notes

Reaction equation

HRID 494728 reaction equation
CCN=C=N[CH2:6][CH2:7][CH2:8]N(C)C.C1C=CC2N(O)N=NC=2C=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]2[C:35]([C:36](O)=[O:37])=[CH:34][N:33]3[C:39]([CH2:42][NH:43][CH2:44]C(OC(C)(C)C)=O)=[CH:40][N:41]=[C:32]3[C:31]=2[Cl:52])=[C:25]([Cl:53])[CH:24]=1.[CH:54]1([CH2:57][O:58][NH2:59])[CH2:56][CH2:55]1.[CH2:60](N(CC)CC)C.[C:67]([O:70]CC)(=[O:69])C>CC(N(C)C)=O>[C:7]([O:70][C:67](=[O:69])[N:43]([CH2:42][C:39]1[N:33]2[CH:34]=[C:35]([C:36](=[O:37])[NH:59][O:58][CH2:57][CH:54]3[CH2:56][CH2:55]3)[C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([Br:22])=[CH:24][C:25]=3[Cl:53])=[C:31]([Cl:52])[C:32]2=[N:41][CH:40]=1)[CH3:44])([CH3:8])([CH3:60])[CH3:6]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 11182605O-(cyclopropylmethyl)hydroxylamineHCID 68861079HCID 68861079, compound

Product 1

HCID 86596994HCID 86596994, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

EDCI (6 mg, 0.033 mmol) and HOBt (5 mg, 0.033 mmol) were added to a solution of 7-(4-bromo-2-chlorophenylamino)-3-[(tert-butoxycarbonylmethylamino)-methyl]-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid (61) in dimethylacetamide (0.4 mL). The yellow solution was allowed to stir at room temperature for 0.5 hours after which time O-cyclopropylmethyl-hydroxylamine (6 mg, 0.066 mmol) and triethylamine (6 μL, 0.044 mmol) were added and the solution allowed to stir overnight. The reaction mixture was diluted with ethyl acetate, washed with water, saturated aqueous ammonium chloride, saturated aqueous potassium carbonate and brine. The organic phase was dried over NaSO4, filtered, concentrated in vacuo to provide the desired product as a yellow residue (11.5 mg, 85%). MS (APCI+) m/z 612, 614, 616 (M+; Cl, Br pattern) detected.

Workup

  1. additionwere added
  2. washwashed with water, saturated aqueous ammonium chloride, saturated aqueous potassium carbonate and brine
  3. dry with materialThe organic phase was dried over NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d57bdedeb8784607af510027bde66eae
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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