Triethylamine → HCID 59590131, compound

HRID 1054391Notes

Reaction equation

HRID 1054391 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 (10 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-315f8b6ef662454bb70231baf587d139
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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