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Acetic Anhydride → HCID 68421046, compound

HRID 1817115
Notes
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Reaction equation

HRID 1817115 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19](Cl)[CH:18]=3)[N:13]=2)=[CH:7][CH:6]=1)[CH3:2].[CH3:25][C@H:26]1[NH:31][C@@H:30]([CH3:32])[CH2:29][NH:28][CH2:27]1.CCN(C(C)C)C(C)C.[C:42](OC(=O)C)(=[O:44])[CH3:43]>CN1C(=O)CCC1.C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([N:28]4[CH2:29][CH:30]([CH3:32])[N:31]([C:42](=[O:44])[CH3:43])[CH:26]([CH3:25])[CH2:27]4)[CH:18]=3)[N:13]=2)=[CH:7][CH:6]=1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 58883268HCID 58883268, compound

Product 1

HCID 68421046HCID 68421046, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
250 °C

Procedure

To a solution of 500 mg of 4-[1-(2-Chloro-pyridin-4-yl)-1H-[1,2,4]triazol-3-ylamino]-benzoic acid ethyl ester (1.45 mMol, 1 equiv) in 10 mL of NMP was added 400 mg of cis-3,5 dimethyl piperazine (3.50 mMol, 2.41 equiv). The stirred solution was heated to 250° C. via microwave irradiation for 15 min. The crude product was precipitated by pouring into 100 mL of water and isolated by filtration. The crude product was then redissolved in 10 mL of CH2Cl2 and 2 mL of DMF. To the stirred solution was added sequentially 1 mL of Hunig's base and 500 μL of acetic anhydride. After 3 hr at 25° C., the reaction mixture was concentrated to a dark oil and purified by flash chromatography (10:1 CH2Cl2:MeOH), yielding 300 mg of 4-{1-[2-(4-Acetyl-3,5-dimethyl-piperazin-1-yl)-pyridin-4-yl]-1H-[1,2,4]triazol-3-ylamino}-benzoic acid ethyl ester (0.647 mMol, 44% yield) as a white solid. 1H NMR (500 MHz, CDCl3) ∂ 8.44 (1H, s), 8.22 (1H, d), 8.05 (2H, d), 7.61 (3H, m), 7.27 (1H, s), 7.02 (1H, s), 6.86 (1H, d), 4.40 (2H, q), 3.50 (2H, q), 3.40 (2H, m), 3.20 (2H, m), 2.20 (3H, s), 1.40 (6H, m), 1.20 (3H, t) ppm. LC/MS: 2.68 min/464 (M+1).

Workup

  1. customThe crude product was precipitated
  2. additionby pouring into 100 mL of water
  3. customisolated by filtration
  4. concentrationthe reaction mixture was concentrated to a dark oil
  5. custompurified by flash chromatography (10:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-bb54ede0c62c4a42bbc8911c1bc087ff
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07598245B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes