Glycolic Acid → HCID 10849575, compound

HRID 1601863Notes

Reaction equation

HRID 1601863 reaction equation
[NH2:1][C:2]1[C:3]([NH:16][CH3:17])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:7]=1.[C:18]([OH:22])(=O)[CH2:19]O>>[CH2:9]([O:8][C:5]1[N:4]=[C:3]2[N:16]([CH3:17])[C:19]([CH2:18][OH:22])=[N:1][C:2]2=[CH:7][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 757Glycolic AcidHCID 107281183-Amino-6-benzyloxy-2-methylaminopyridine

Product 1

HCID 10849575HCID 10849575, compoundYield 46.5%

Procedure

A procedure similar to that described in Preparation 43 was repeated, except that 7.50 g of 3-amino-6-benzyloxy-2-methylaminopyridine (prepared as described in Preparation 93) and 7.46 g of glycolic acid were reacted. After working up the product as described in Preparation 43, the resulting crude product was purifying by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and methanol as the eluent, and was then crystallized by trituration with ethyl acetate, to give 4.10 g of the title compound, melting at 133-135° C.

Workup

  1. customA procedure similar to that described in Preparation 43
  2. customwere reacted
  3. customas described in Preparation 43
  4. customthe resulting crude product was purifying by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and methanol as the eluent
  6. customwas then crystallized by trituration with ethyl acetate

Sources & evidence

ORD record
ord-62743e3765a04615b2050e03c8f73ef2
Source dataset
uspto-grants-1999_11
Patent number
US05977365

Reaction notes

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