Triethylamine → HCID 86596994, compound

HRID 1788252Notes

Reaction equation

HRID 1788252 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-20dc90001c9a415da8c5a6b5eb7186bb
Source dataset
uspto-grants-2009_03
Patent number
US07511058B2

Reaction notes

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