Triethylamine → HCID 59680016, compound

HRID 2265058Notes

Reaction equation

HRID 2265058 reaction equation
Cl[CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O.C(N(CC)CC)C.[C:28]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>C(Cl)Cl>[C:31]([O:30][C:28]([N:35]1[CH2:40][CH2:39][N:38]([CH2:2][C:3]2[N:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]3=[N:5][C:4]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:37][CH2:36]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 59679846HCID 59679846, compound

Product 1

HCID 59680016HCID 59680016, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 3-Chloromethyl-2-(2-nitro-phenyl)-imidazo[1,2-a]pyridine (298 mg, 0.92 mmol) suspended in CH2Cl2 (15 ml) cooled to 0° C. was added dropwise triethylamine (279 mg, 3 eq), followed by 1-Boc-piperazine (1.3 eq, 221 mg) in two portions over a 24 hour period. The reaction mixture was concentrated to dryness and purified by chromatography using a 9:1 mixture of CH2Cl2 to MeOH. The fractions were concentrated, dissolved in Ethanol (20 ml), and stirred over H2 atmosphere with 10% Pd/C (10 mg) for 48 hours. The reaction mixture was filtered through Celite and concentrated, and dried under high vacuum to obtain 250 mg of the desired product. (MS, M++H=408.2)

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by chromatography
  3. additiona 9:1 mixture of CH2Cl2 to MeOH
  4. concentrationThe fractions were concentrated
  5. dissolutiondissolved in Ethanol (20 ml)
  6. filtrationThe reaction mixture was filtered through Celite
  7. concentrationconcentrated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-5a76aa8dac11412695062dd8f6421c2d
Source dataset
uspto-grants-2010_12
Patent number
US07855289B2

Reaction notes

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