Hydrochloric Acid → 1-[({3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}amino)methyl]cyclopropanol

HRID 41276

Reaction equation

HRID 41276 reaction equation
O1CCCC1.[CH3:6][O:7][C:8]1[CH:13]=[C:12]([CH2:14][O:15][CH3:16])[CH:11]=[C:10]([O:17][CH3:18])[C:9]=1[C:19]1[N:20]2[N:26]=[C:25]([O:27][CH3:28])[C:24]([NH:29][C:30]([C:32]3([OH:35])[CH2:34][CH2:33]3)=O)=[C:21]2[S:22][CH:23]=1.B#B.Cl>CCCCCCC.C(OCC)(=O)C.O>[CH3:18][O:17][C:10]1[CH:11]=[C:12]([CH2:14][O:15][CH3:16])[CH:13]=[C:8]([O:7][CH3:6])[C:9]=1[C:19]1[N:20]2[N:26]=[C:25]([O:27][CH3:28])[C:24]([NH:29][CH2:30][C:32]3([OH:35])[CH2:33][CH2:34]3)=[C:21]2[S:22][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 6328200DiboronHCID 67095311N-{3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}-1-hydroxycyclopropanecarboxamide

Product 1

HCID 670956311-[({3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}amino)methyl]cyclopropanolYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899848Ethylacetate heptaneSolvent

Conditions

Temperature
55 °C

Procedure

To a tetrahydrofuran (4 mL) solution of N-{3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl}-1-hydroxycyclopropanecarboxamide (162 mg, 0.374 mmol) was added 0.99 M diborane (0.944 mL, 0.935 mmol), and the mixture was stirred at 55° C. for two hours. The temperature was made to be room temperature, and a 2N aqueous solution of hydrochloric acid (0.374 mL, 0.748 mmol) was added, and the mixture was stirred at 50° C. for one hour. Water was added to the reaction mixture at room temperature, and the reaction mixture was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column (NI-1) chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=1/1) to obtain the title compound (94.5 mg, 0.225 mmol).

Workup

  1. customto be room temperature
  2. stirringthe mixture was stirred at 50° C. for one hour
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. distillationthe solvent in the filtrate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column (NI-1) chromatography (a mixed solvent of n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-bab7c4ba35724f5c97dc32f6ad89db93
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Linked notes

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