4-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid → HCID 86666024, compound

HRID 1802258Notes

Reaction equation

HRID 1802258 reaction equation
Cl.[F:2][CH2:3][CH2:4][N:5]([CH3:16])[C:6]1[N:15]=[C:9]2[CH:10]=[C:11]([NH2:14])[CH:12]=[CH:13][N:8]2[N:7]=1.[CH2:17]([O:19][C:20]([C:22]1[CH:26]=[N:25][N:24]([CH3:27])[C:23]=1[C:28](O)=[O:29])=[O:21])[CH3:18]>>[CH2:17]([O:19][C:20]([C:22]1[CH:26]=[N:25][N:24]([CH3:27])[C:23]=1[C:28](=[O:29])[NH:14][C:11]1[CH:12]=[CH:13][N:8]2[N:7]=[C:6]([N:5]([CH2:4][CH2:3][F:2])[CH3:16])[N:15]=[C:9]2[CH:10]=1)=[O:21])[CH3:18]

Participants

3

Reactant 2

HCID 252475674-(Ethoxycarbonyl)-1-methyl-1H-pyrazole-5-carboxylic acidHCID 86666021HCID 86666021, compound

Product 1

HCID 86666024HCID 86666024, compoundYield 76.2%

Procedure

The product was prepared in the same manner as described in example 65c) using N2-(2-fluoro-ethyl)-N2-methyl-[1,2,4]triazolo[1,5-a]pyridine-2,7-diamine hydrochloride (1.3 g, 5.3 mmol) and 2-methyl-2H-pyrazole-3,4-dicarboxylic acid-4-ethyl ester (1.08 g, 5.45 mmol) as starting materials. The solvent was evaporated and the resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution. The precipitated solid was filtered off, washed with water 4 times and dried in vacuo affording 5-{2-[(2-fluoro-ethyl)-methyl-amino]-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamoyl}-1-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.57 g, 76.2%) as a light yellow solid. MS: m/z=390.5 (M+H+).

Workup

  1. customThe product was prepared in the same manner
  2. customThe solvent was evaporated
  3. customthe resulting yellowish oil was triturated with sat. sodium hydrogencarbonate solution
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with water 4 times
  6. customdried in vacuo

Sources & evidence

ORD record
ord-7b01a6b27d0a46c6a5e33dd79b41b4c2
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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