Dichloromethane → HCID 85418533, compound

HRID 1817119Notes

Reaction equation

HRID 1817119 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:13]=[CH:12][N:11]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH:24]([CH3:26])[N:23]([C:27](=[O:29])[CH3:28])[CH:22]([CH3:30])[CH2:21]4)[CH:15]=3)[N:10]=2)=[CH:4][CH:3]=1.C(Cl)Cl.CCN(C(C)C)C(C)C.[O:43]1[CH:47]=[CH:46][CH:45]=[C:44]1Cl.CN1[C:54](=[O:55])CCC1>>[C:27]([N:23]1[CH:24]([CH3:26])[CH2:25][N:20]([C:16]2[CH:15]=[C:14]([N:11]3[CH:12]=[N:13][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([NH:1][C:54]([C:44]5[O:43][CH:47]=[CH:46][CH:45]=5)=[O:55])=[CH:3][CH:4]=4)=[N:10]3)[CH:19]=[CH:18][N:17]=2)[CH2:21][CH:22]1[CH3:30])(=[O:29])[CH3:28]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 1378562-ChlorofuranHCID 21106440HCID 21106440, compound

Product 1

HCID 85418533HCID 85418533, compoundYield 2.3%

Procedure

To a solution of 50 mg of 1-(4-{4-[3-(4-Amino-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-yl}-2,6-dimethyl-piperazin-1-yl)-ethanone (0.123 mMol. 1.00 equiv) in 2 mL of NMP was added 5 mL of CH2Cl2 and 500 μL of Hunig's base followed by 100 μL of 2-furanyl chloride (1.01 mMol, 8.13 equiv). The reaction mixture was stirred for 1 hr and concentrated. The resulting oil was purified via flash chromatography (EtOAc) to yield 1.4 mg of Furan-2-carboxylic acid (4-{1-[2-(4-acetyl-3,5-dimethyl-piperazin-1-yl)-pyridin-4-yl]-1H-[1,2,4]triazol-3-ylamino}-phenyl)-amide (0.0028 mMol, 2.3% yield). 1H NMR (500 MHz, MeOD-d4) ∂ 8.95 (1H, s), 8.18 (1H, d), 7.72 (1H, m), 7.61 (4H, m), 7.25 (2H, m), 7.15 (1H, m), 6.61 (1H, s), 4.30 (2H, m), 3.30 (2H, m), 3.15 (2H, m), 2.20 (3H, s), 1.35 (6H, m) ppm. LC/MS: 2.2 min/501.3 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe resulting oil was purified via flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-ce56141d59f04154866ba6d1073a987c
Source dataset
uspto-grants-2009_10
Patent number
US07598245B2

Reaction notes

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