Glycolic Acid → HCID 10849575, compound

HRID 1599329Notes

Reaction equation

HRID 1599329 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-40823409d557477c965f175e40cba542
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

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