Triethylamine → HCID 59589972, compound

HRID 1472847Notes

Reaction equation

HRID 1472847 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-455931b48a214889b5de9757fbadde40
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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