Potassium Carbonate → HCID 178509205, compound

HRID 1472861Notes

Reaction equation

HRID 1472861 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:36]=[C:19]4[CH:20]=[CH:21][CH:22]=[C:23]([C:24]5[CH:25]=[N:26][N:27]([CH2:29][CH2:30]OS(C)(=O)=O)[CH:28]=5)[N:18]4[N:17]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[NH2:43][C:44]1[N:48]=[C:47]([SH:49])[NH:46][N:45]=1>CN(C)C=O>[NH2:43][C:44]1[NH:48][C:47]([S:49][CH2:30][CH2:29][N:27]2[CH:28]=[C:24]([C:23]3[N:18]4[N:17]=[C:16]([NH:15][C:12]5[CH:11]=[CH:10][C:9]([O:8][CH2:7][CH2:6][N:1]6[CH2:5][CH2:4][CH2:3][CH2:2]6)=[CH:14][CH:13]=5)[N:36]=[C:19]4[CH:20]=[CH:21][CH:22]=3)[CH:25]=[N:26]2)=[N:46][N:45]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59589683Methanesulfonic acid 2-(4-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-ethyl esterHCID 1785092965-amino-1H-1,2,4-triazole-3-thiol

Product 1

HCID 178509205HCID 178509205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methanesulfonic acid 2-(4-{2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-5-yl}-pyrazol-1-yl)-ethyl ester (0.40 g, 0.78 mmol) in dimethylformamide (1 ml) was added potassium carbonate (150 mg) followed by 3-amino-5-mercapto-1,2,4-triazole (19 mg, 0.156 mmol). The mixture was stirred for 18 hours at room temperature, then filtered and concentrated in vacuo. The title compound was purified by preparatory HPLC to yield the desired product. LCMS method: 2, RT: 2.15 min, MI: 532 [M+1]; 1H NMR (300 MHz, DMSO) 9.35 (s, 1H), 8.81 (s, 1H), 8.45 (s, 1H), 8.22 (s, 2H), 7.58 (d, 2H), 7.55 (d, 1H), 7.40 (dd, 2H), 6.85 (d, 2H), 6.13 (s, 1H), 4.51 (t, 2H), 3.98 (t, 2H), 3.48 (t, 2H), 2.75 (t, 2H), 2.49 (s, 4H), 1.65 (s, 4H).

Workup

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

Sources & evidence

ORD record
ord-f35ba1f0be814ddb933fd601eaa0bb35
Source dataset
uspto-grants-2015_04
Patent number
US09012633B2

Reaction notes

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