Triethylamine → HCID 59590131, compound

HRID 1971579Notes

Reaction equation

HRID 1971579 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:20][CH:19]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:32]([N:34](CC)CC)C.[C:39](Cl)(=[O:44])[CH2:40][CH:41]([CH3:43])[CH3:42]>ClCCl>[CH3:42][CH:41]([CH3:43])[CH2:40][C:39]([NH:34][CH2:32][C:3]1[CH:2]=[CH:7][CH:6]=[C:5]([C:8]2[N:13]3[N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:20][CH:19]=4)[N:16]=[C:12]3[CH:11]=[CH:10][CH:9]=2)[CH:4]=1)=[O:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66054Isovaleryl chlorideHCID 68705150HCID 68705150, compound

Product 1

HCID 59590131HCID 59590131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of [5-(4-amino-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (0.03 g, 0.07 mmol) and triethylamine (11 μl, 0.077 mmol) in dichloromethane (1 ml) was added isovaleryl chloride (100 μl, 0.077 mmol). The mixture was stirred for 18 hours at room temperature, then filtered through a plug of silica, washed with methanol and concentrated in vacuo. The crude was purified by preparatory HPLC to give the desired product. LCMS RT: 2.54 min, MI: 513, Method: 2; 1H NMR (DMSO, 300 MHz): 9.37 (s, 1H), 8.38 (t, 1H), 8.18 (s, 1H), 7.89 (s, 1H), 7.56 (m, 4H), 7.40 (d, 1H), 7.08 (d, 1H), 6.85 (d, 2H), 4.36 (d, 2H), 3.98 (t, 2H), 2.79 (t, 2H), 2.55 (s, 4H), 1.98 (s, 2H), 1.66 (s, 5H), 0.82 (s, 6H).

Workup

  1. filtrationfiltered through a plug of silica
  2. washwashed with methanol
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by preparatory HPLC

Sources & evidence

ORD record
ord-02d59728a5eb4db49e03884d37f20787
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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