Benzoyl chloride → HCID 59589807, compound

HRID 1971573Notes

Reaction equation

HRID 1971573 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-e3330287d42d42ba9cf9da4984f43181
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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