Benzoyl chloride → HCID 59589807, compound

HRID 1054385Notes

Reaction equation

HRID 1054385 reaction equation
[NH2:1][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.C(N(CC)CC)C.[C:39](Cl)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>ClCCl>[N:27]1([CH2:26][CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([NH:17][C:15]3[N:16]=[C:12]4[CH:11]=[CH:10][CH:9]=[C:8]([C:5]5[CH:6]=[CH:7][C:2]([NH:1][C:39](=[O:46])[C:40]6[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=6)=[CH:3][CH:4]=5)[N:13]4[N:14]=3)=[CH:19][CH:20]=2)[CH2:28][CH2:29][CH2:30][CH2:31]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 68705150HCID 68705150, compound

Product 1

HCID 59589807HCID 59589807, 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 (0.05 g, 0.121 mmol) and triethylamine (19 μl, 0.133 mmol) in dichloromethane (1 ml) was added benzoyl chloride (17 μl, 0.133 mmol). The mixture was stirred for 18 hours at room temperature, then filtered through a plug of silica, washed with methanol and the filtrates combined and concentrated in vacuo. The product was purified by preparatory LCMS to provide the desired product. RT: 2.77 min, MI: 519, Method: 2; 1H NMR (DMSO, 300 MHz): 8.62 (s, 1H), 8.07 (2H, d), 7.97 (2H, d), 7.92 (d, 2H) 7.54-7.41 (m, 5H), 7.01 (1H, d), 6.85 (d, 2H), 4.31 (t, 2H), 3.37 (t, 2H), 3.26 (s, 4H), 3.12 (s, 1H), 2.99 (s, 1H), 2.02 (s, 4H).

Workup

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

Sources & evidence

ORD record
ord-9c0c1cd8babe46309ac83cab6dbe8c3c
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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