Triethylamine → HCID 59589972, compound

HRID 1971581Notes

Reaction equation

HRID 1971581 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[CH:21][CH:20]=4)[N:17]=[C:13]3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH2:40]([S:44](Cl)(=[O:46])=[O:45])[CH2:41][CH2:42][CH3:43]>ClCCl>[N:28]1([CH2:27][CH2:26][O:25][C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:16]3[N:17]=[C:13]4[CH:12]=[CH:11][CH:10]=[C:9]([C:5]5[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=5)[CH2:2][NH:1][S:44]([CH2:40][CH2:41][CH2:42][CH3:43])(=[O:46])=[O:45])[N:14]4[N:15]=3)=[CH:20][CH:21]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 754301-Butanesulfonyl chlorideHCID 59589633[5-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine

Product 1

HCID 59589972HCID 59589972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of [5-(3-aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (0.03 g, 0.070 mmol) in dichloromethane (1 ml) was added triethylamine (13 μl, 0.091 mmol) followed by butanesulfonyl chloride (11 μl, 0.084 mmol). The mixture was stirred for 18 hours at room temperature, then filtered and concentrated in vacuo. The product was purified by preparatory HPLC to provide the desired product. LCMS RT: 2.66 min, MI: 549, Method: 2; 1H NMR (DMSO, 300 MHz): 9.43 (s, 1H), 8.18 (s, 1H), 8.03 (d, 1H), 7.65 (m, 6H), 7.16 (d, 1H), 6.90 (d, 2H), 4.27 (d, 2H), 4.05 (t, 2H), 2.93 (t, 2H), 2.70 (s, 4H), 2.45 (dd, 2H), 1.74 (s, 4H), 1.59 (m, 2H), 1.28 (m, 2H), 0.82 (m, 3H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe product was purified by preparatory HPLC

Sources & evidence

ORD record
ord-5e92c992ae214946a8061b891c3d43b4
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

Loading…