Triethylamine → HCID 86596994, compound

HRID 1766815Notes

Reaction equation

HRID 1766815 reaction equation
CCN=C=N[CH2:6][CH2:7][CH2:8]N(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[Br:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]2[C:36]([C:37](O)=[O:38])=[CH:35][N:34]3[C:40]([CH2:43][NH:44][CH2:45]C(OC(C)(C)C)=O)=[CH:41][N:42]=[C:33]3[C:32]=2[Cl:53])=[C:26]([Cl:54])[CH:25]=1.[CH:55]1([CH2:58][O:59][NH2:60])[CH2:57][CH2:56]1.[CH2:61](N(CC)CC)C.[C:68]([O:71]CC)(=[O:70])C>CC(N(C)C)=O>[C:7]([O:71][C:68](=[O:70])[N:44]([CH2:43][C:40]1[N:34]2[CH:35]=[C:36]([C:37](=[O:38])[NH:60][O:59][CH2:58][CH:55]3[CH2:57][CH2:56]3)[C:31]([NH:30][C:27]3[CH:28]=[CH:29][C:24]([Br:23])=[CH:25][C:26]=3[Cl:54])=[C:32]([Cl:53])[C:33]2=[N:42][CH:41]=1)[CH3:45])([CH3:8])([CH3:61])[CH3:6]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11182605O-(cyclopropylmethyl)hydroxylamineHCID 68861079HCID 68861079, compound

Product 1

HCID 86596994HCID 86596994, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

EDCl (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-chloro-imidazo[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-790ff9c20c7142e5841a3438deb7d390
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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