Triethylamine → HCID 59590131, compound

HRID 1472845Notes

Reaction equation

HRID 1472845 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-19a68705916a4b6686ad34549098385b
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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