Potassium Carbonate → HCID 178509205, compound

HRID 1971595Notes

Reaction equation

HRID 1971595 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-7ed7733526ab48d09aabf60a495d2d5c
Source dataset
uspto-grants-2013_04
Patent number
US08431596B2

Reaction notes

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