Benzene, 1-chloro-3-isocyanato- → 1-(3-Chloro-phenyl)-3-(3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzyl)-urea

HRID 1054392Notes

Reaction equation

HRID 1054392 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.[Cl:33][C:34]1[CH:35]=[C:36]([N:40]=[C:41]=[O:42])[CH:37]=[CH:38][CH:39]=1>ClCCl>[Cl:33][C:34]1[CH:35]=[C:36]([NH:40][C:41]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([C:9]3[N:14]4[N:15]=[C:16]([NH:18][C:19]5[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]6[CH2:29][CH2:30][CH2:31][CH2:32]6)=[CH:21][CH:20]=5)[N:17]=[C:13]4[CH:12]=[CH:11][CH:10]=3)[CH:4]=2)=[O:42])[CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 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 595901461-(3-Chloro-phenyl)-3-(3-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-benzyl)-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[5-(3-Aminomethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-[4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-amine (40 mg, 0.093 mmol) was dissolved in dichloromethane (1 ml). 3-Chlorophenyl isocyanate (13 μl, 0.103 mmol) was added and the mixture stirred overnight. The solvent was removed under reduced pressure and the product was purified by preparatory HPLC to give the desired product. LCMS RT: 2.86 min, MI: 582, Method: 2. 1H NMR (DMSO, 300 MHz): 9.38 (s, 1H), 8.99 (s, 1H), 8.16 (s, 1H), 7.96 (s, 1H), 7.86 (d, 1H), 7.66-7.49 (m, 5H), 7.17 (d, 2H), 7.11 (d, 1H), 7.01 (t, 1H), 6.84 (d, 2H), 4.39 (d, 2H), 3.98 (t, 2H), 2.81 (t, 2H), 2.53 (s, 4H), 1.67 (s, 4H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product was purified by preparatory HPLC

Sources & evidence

ORD record
ord-8907eaacb97a4e3da017637144373cc4
Source dataset
uspto-grants-2016_07
Patent number
US09394301B2

Reaction notes

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