Triethylamine → HCID 59680016, compound

HRID 1667053Notes

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

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

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

Sources & evidence

ORD record: ord-a601efb47d5a40448e9f04eeb0158483
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044198B2

Reaction notes

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