Aniline → HCID 57500679, compound

HRID 1919658Notes

Reaction equation

HRID 1919658 reaction equation
Cl[C:2]1[C:11]2[N:12]=[CH:13][S:14][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:15]([O:17]C)=[O:16])=[CH:5][C:4]=2[N:3]=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN1C(=O)CCC1>[C:20]1([NH:19][C:2]2[C:11]3[N:12]=[CH:13][S:14][C:10]=3[C:9]3[CH:8]=[CH:7][C:6]([C:15]([OH:17])=[O:16])=[CH:5][C:4]=3[N:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 57500678HCID 57500678, compound

Product 1

HCID 57500679HCID 57500679, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

In a microwave vessel, methyl 4-chlorothiazolo[4,5-c]quinoline-7-carboxylate (1.0 eq, 23 mg, 0.084 mmol) and aniline (13 eq, 0.1 ml, 1.1 mmol) were mixed in NMP (0.1 ml). The mixture was heated in a microwave oven at 120° C. for 10 min. The intermediate ester was purified by preparative HPLC and isolated as a solid after genevac evaporation. The solid was stirred in a (1:1:1, v:v:v) mixture of THF, MeOH and water (0.6 ml) with LiOH (41 mg) at room temperature for 2 hours. HCl and water were added, the organic solvents were evaporated and the solution allowed resting for 2 hours. The precipitate that slowly formed was filtered and dried to afford 4-(phenylamino)thiazolo[4,5-c]quinoline-7-carboxylic acid as a solid (8% yield over 2 steps). LCMS (ES): >95% pure, m/z 322 [M+1]+.

Workup

  1. customThe intermediate ester was purified by preparative HPLC
  2. customisolated as a solid
  3. customafter genevac evaporation
  4. additionHCl and water were added
  5. customthe organic solvents were evaporated
  6. waitthe solution allowed resting for 2 hours
  7. customThe precipitate that slowly formed
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-09bc8835bb1b488599ec6194b477dc17
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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