Benzyl bromoacetate → HCID 89726362, compound

HRID 1777754Notes

Reaction equation

HRID 1777754 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][N:6]([C:10](OC(C)(C)C)=O)[CH2:5][C:4]=2[CH:3]=[N:2]1.Br[CH2:18][C:19]([O:21]CC1C=CC=CC=1)=[O:20]>>[CH3:10][N:6]1[CH2:7][CH2:8][C:9]2=[N:1][N:2]([CH2:18][C:19]([OH:21])=[O:20])[CH:3]=[C:4]2[CH2:5]1

Participants

3

Reactant 2

HCID 62576Benzyl bromoacetateHCID 103986805-Boc-1,4,6,7-tetrahydropyrazolo[4,3-C]pyridine

Product 1

HCID 89726362HCID 89726362, compound

Procedure

tert-Butyl 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (500 mg) was submitted to alkylation with benzyl bromoacetate, followed by cleavage of the Boc protecting group and subsequent methylation of the free amine using a method analogous to that of Precursor for Example 209 step 209.2 to step 209.4. However, the mixture of regioisomers was separated at the end of the three steps (Biotage, DCM/MeOH/TEA) to afford the two isomers:

Workup

  1. additionHowever, the mixture of regioisomers
  2. customwas separated at the end of the three steps (Biotage, DCM/MeOH/TEA)
  3. customto afford the two isomers

Sources & evidence

ORD record
ord-25050d4912a64d21874c1bdc3de8511c
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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