1-Pyrrolidineethanamine → HCID 57484107, compound

HRID 720788Notes

Reaction equation

HRID 720788 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][C:15]=2[C:16]([NH2:18])=[O:17])[N:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[N:11]=[CH:10]3)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:37]1([CH2:42][CH2:43]N)[CH2:41][CH2:40][CH2:39][CH2:38]1>C1COCC1>[N:37]1([CH2:42][CH2:43][NH:18][C:16]([C:15]2[CH:14]=[C:13]3[C:9]([CH:10]=[N:11][N:12]3[CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:8][C:7]=2[O:6][C:5]2[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=2)=[O:17])[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 13441-PyrrolidineethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 574187391h-Indazole-6-carboxamide,5-(4-fluorophenoxy)-1-(2-methylpropyl)-2×

Product 1

HCID 57484107HCID 57484107, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (compound 10g, prepared as described in Example 46) in THF was treated with carbonyldiimidazole (1.2 equivalents) at room temperature under nitrogen atmosphere. After stirring for 18 hours, the reaction was treated with 2-pyrrolidin-1-yl-ethylamine (1 equivalent). After an additional 18 hours, the solvent was allowed to slowly evaporate and the residue was purified in a Sep Pak cartridge eluting with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2 to provide compound 11g-7 as an oil in 63% yield.

Workup

  1. waitAfter an additional 18 hours
  2. customto slowly evaporate
  3. customthe residue was purified in a Sep Pak cartridge
  4. washeluting with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2
  5. customto provide compound 11g-7 as an oil in 63% yield

Sources & evidence

ORD record
ord-4d089fbe9b414329b6638e9e98ea1c29
Source dataset
uspto-grants-2006_11
Patent number
US07135575B2

Reaction notes

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