Diisopropylethylamine → HCID 21106443, compound

HRID 1765056Notes

Reaction equation

HRID 1765056 reaction equation
[C:1]1([NH:7][C:8]2[N:12]=[CH:11][N:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[CH:29]1([CH2:34][C:35](Cl)=[O:36])[CH2:33][CH2:32][CH2:31][CH2:30]1>CN1C(=O)CCC1>[CH:29]1([CH2:34][C:35]([NH:19][C:15]2[CH:14]=[C:13]([N:10]3[CH:11]=[N:12][C:8]([NH:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:9]3)[CH:18]=[CH:17][N:16]=2)=[O:36])[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3485182Cyclopentylacetyl chlorideHCID 21106452HCID 21106452, compound

Product 1

HCID 21106443HCID 21106443, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

4-(3-Phenylamino-[1,2,4]triazol-1-yl)-pyridin-2-ylamine (50 mg, 0.20 mMol) was dissolved in 2.5 mL of NMP with (50 μL, 67.4 mg, 0.52 mMol) of Hunig's base and (30 μL, 32 mg, 0.2 mMol) of cyclopentylmethyl carbonyl chloride. The reaction was stirred at ambient temperature for 18 hr. LC shows starting material, mono acylated material, and a majority of the bis acylated imide. Another alliquot of the acylating agent was added and the reaction was stirred until all starting material was consumed. Five drops of 2.0N sodium hydroxide was then added and the reaction was stirred for ten hours at ambient temperature, until all of the imide was hydrolyzed. The reaction mixture was acidified with TFA and the crude material was purified via HPLC, C18 silica with a gradient of acetonitrile/water/0.1% TFA as the eluent. Yield˜13 mg of a pale yellow powder as the TFA salt; (18%). 1H NMR 500 MHz (DMSO-d6) ∂ 1.29m, 2H), 1.5(m, 2H), 1.77(m, 2H), 2.25(m, 1H), 2.4(d, 2H), 6.88(t, 1H), 7.28(t, 2H), 7.53(d, 1H), 7.63(d, 2H), 8.35(d, 1H), 8.55(d, 1H), 9.2(s, 1H), 9.57(s, 1H), 10.6(s ex, 1H). LC/MS [M+H+] 363

Workup

  1. additionAnother alliquot of the acylating agent was added
  2. stirringthe reaction was stirred until all starting material
  3. customwas consumed
  4. additionFive drops of 2.0N sodium hydroxide was then added
  5. stirringthe reaction was stirred for ten hours at ambient temperature
  6. customthe crude material was purified via HPLC

Sources & evidence

ORD record
ord-9ef6291690d64dd392b284e4d9c0857b
Source dataset
uspto-grants-2007_06
Patent number
US07226920B2

Reaction notes

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