Acetic Acid → HCID 10223336, compound

HRID 427305Notes

Reaction equation

HRID 427305 reaction equation
F[C:2](F)(F)C(O)=O.[C:8]([C:10]1[CH:14]=[N:13][N:12]([CH3:15])[C:11]=1[NH:16][C:17]([C:19]1[C:27]2[S:26][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:24][C:23]=2[C:22]([O:34][CH3:35])=[CH:21][CH:20]=1)=[O:18])#[N:9].C=O.C([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[C:8]([C:10]1[CH:14]=[N:13][N:12]([CH3:15])[C:11]=1[NH:16][C:17]([C:19]1[C:27]2[S:26][C:25]([N:28]3[CH2:33][CH2:32][N:31]([CH3:2])[CH2:30][CH2:29]3)=[N:24][C:23]=2[C:22]([O:34][CH3:35])=[CH:21][CH:20]=1)=[O:18])#[N:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10185913HCID 10185913, compound

Product 1

HCID 10223336HCID 10223336, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-methoxy-2-(piperazin-1-yl)benzothiazole-7-carboxylic acid (4-cyano-2-methyl-2H-pyrazol-3-yl)amide trifluoroacetic acid salt (275 mg) in acetonitrile (20 ml) was treated with formaldehyde (0.44 ml, 37% aqueous solution), sodium cyanoborohydride (102 mg), and acetic acid (0.3 ml) and the mixture stirred at room temperature of 12 hours. The solvent was evaporated in vacuao and the residue partitioned between aqueous sodium hydroxide (10 ml, 1M) and dichloromethane (100 ml). The aqueous layer was separated, was neutralised with acetic acid, and extracted with 2% methanol in dichloromethane (2×75 ml). The extracts were combined, dried over magnesium sulphate (5 g), filtered, and the filtrate evaporated in vacuo. Purification by column chromatography (eluent 5% methanol in dichloromethane) followed by trituration with diethyl ether yielded the title compound as a pale yellow solid (40 mg). TLC Rf 0.14 (10% methanol in dichloromethane); Mpt 249-251° C.

Workup

  1. customThe solvent was evaporated in vacuao
  2. customthe residue partitioned between aqueous sodium hydroxide (10 ml, 1M) and dichloromethane (100 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with 2% methanol in dichloromethane (2×75 ml)
  5. dry with materialdried over magnesium sulphate (5 g)
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customPurification by column chromatography (eluent 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5b94259e7c8e48a28fac751849ec6c19
Source dataset
uspto-grants-2001_11
Patent number
US06313116B1

Reaction notes

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