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Citric Acid → HCID 19756390, compound

HRID 1587834
Notes
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Reaction equation

HRID 1587834 reaction equation
CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:19]([C:21]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[N:46]=[N:47][N:48]([C:50]([C:63]4[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=4)([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:49]=3)=[CH:35][CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:69][CH2:70][CH2:71][OH:72])[N:27]=2)[N:22]=1)[CH3:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(N(CC)CC)C>[CH2:19]([C:21]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[N:46]=[N:47][N:48]([C:50]([C:63]4[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=4)([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:49]=3)=[CH:37][CH:38]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:69][CH2:70][CH:71]=[O:72])[N:27]=2)[N:22]=1)[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 14812Phosphorus oxide (P4O10)HCID 19756350HCID 19756350, compound

Product 1

HCID 19756390HCID 19756390, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8471TriethylamineSolvent

Procedure

DMSO (2.0 ml) and phosphorus pentoxide (4.0 g) were added to a solution of 2-ethyl-6-(2-hydroxyethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in dichloromethane (20 ml) at 0° C. The mixture was stirred at ambient temperature for 1 hour and then cooled again to 0° C. Triethylamine (0.69 ml) was added and stirring was continued for 30 minutes. 1M citric acid solution (20 ml) was added and the organic phase was separated and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give 2-ethyl-6-(formylmethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (B) (0.46 g), m.p. 168°-169° C. (after trituration with ether; NMR (d6 -DMSO): 1.25(t, 3H), 2.9(q, 2H), 5.0(s, 2H), 5.35(s, 2H), 6.8-6.95(m, 6H), 7.1-7.85(m, 19H), 8.25(d, 1H), 9.7(s, 1H).

Workup

  1. temperaturecooled again to 0° C
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. customthe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:1 v/v)

Sources & evidence

ORD record
ord-55ea0ede57154d598131d0251116df29
Source dataset
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05219863

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes