Pyridine → HCID 57906441, compound

HRID 420544Notes

Reaction equation

HRID 420544 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:24][N:25]=[C:11]2[CH:10]=1)(C)(C)C.[C:33](Cl)(=[O:35])[CH3:34].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:7][CH2:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])=[CH:13][N:12]2[C:23]([N:26]3[CH2:27][CH2:28][N:29]([C:33](=[O:35])[CH3:34])[CH2:30][CH2:31]3)=[CH:24][N:25]=[C:11]2[CH:10]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 57906493HCID 57906493, compound

Product 1

HCID 57906441HCID 57906441, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [6-(2,4-dichloro-phenyl)-3-piperazin-1-yl-imidazo[1,2-a]pyridin-7-ylmethyl]-carbamic acid tert-butyl ester (30 mg, 0.06 mmol) in DCM (0.5 mL) were added successively acetyl chloride (6 mg, 0.07 mmol), pyridine (0.015 mL, 0.19 mmol) and DMAP (1 mg, 0.006 mmol). The reaction mixture was stirred at RT for 14 h then evaporated to dryness. The resulting residue was dissolved in DCM (2 mL) then TFA (1 mL) was added and the mixture was stirred at RT for 30 min. The reaction mixture was concentrated to dryness and the remaining residue purified by reverse phase prep-HPLC (Waters system) to give the title compound (2TFA salt, 22 mg, 0.034 mmol, 57% for 2 steps) as a white solid. MS: 419 [M+1]+; HPLC: AtRet=1.00.

Workup

  1. customthen evaporated to dryness
  2. dissolutionThe resulting residue was dissolved in DCM (2 mL)
  3. additionTFA (1 mL) was added
  4. stirringthe mixture was stirred at RT for 30 min
  5. concentrationThe reaction mixture was concentrated to dryness
  6. customthe remaining residue purified by reverse phase prep-HPLC (Waters system)

Sources & evidence

ORD record
ord-adf1d230de9c4359ad61a4c876ed2ebe
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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