Acetic Acid → HCID 66689887, compound

HRID 337134Notes

Reaction equation

HRID 337134 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([NH:14][C:15]1[C:16](=[O:35])[N:17]([C:21]2[CH:22]=[C:23]([CH:30]=[C:31]([F:34])[C:32]=2[CH3:33])[C:24]([NH:26][CH:27]2[CH2:29][CH2:28]2)=[O:25])[CH:18]=[CH:19][N:20]=1)([CH3:13])[CH3:12].C(N(CC)CC)C.Br[CH2:44][C:45]([O:47]C)=[O:46].C(O)(=O)C>C1COCC1.[OH-].[Na+].CO>[CH:27]1([NH:26][C:24]([C:23]2[CH:30]=[C:31]([F:34])[C:32]([CH3:33])=[C:21]([N:17]3[CH:18]=[CH:19][N:20]=[C:15]([NH:14][C:11]([C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=4[O:4][CH2:3][CH2:2][NH:1][CH2:44][C:45]([OH:47])=[O:46])([CH3:12])[CH3:13])[C:16]3=[O:35])[CH:22]=2)=[O:25])[CH2:28][CH2:29]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 25143767HCID 25143767, compound

Product 1

HCID 66689887HCID 66689887, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-(3-(2-(2-(2-aminoethoxy)phenyl)propan-2-ylamino)-2-oxopyrazin-1(2H)-yl)-N-cyclopropyl-5-fluoro-4-methylbenzamide (Example 311, 0.17 g) dissolved in THF (10 mL) was treated with triethylamine (0.049 mL) and methyl bromoacetate (0.034 mL) under nitrogen. The resulting mixture was stirred at 20° C. for 16 h. The reaction mixture was diluted with 2M aqueous NaOH (2 mL) and methanol (2 mL). The solution was stirred at room temperature for 1 h, acidified with acetic acid and extracted with ethyl acetate (50 mL).

Workup

  1. stirringThe solution was stirred at room temperature for 1 h
  2. extractionextracted with ethyl acetate (50 mL)

Sources & evidence

ORD record
ord-ca3eac96fb0c4283bcbff3724a3e2699
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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