Triethylamine → [3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-carbamic acid phenyl ester

HRID 38077Notes

Reaction equation

HRID 38077 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8]([C:16]3[CH:17]=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=3)=[N:9][N:10]3[CH2:15][CH2:14][CH2:13][S:12][C:11]=23)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:30]1([O:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[C:30]1([O:36][C:37](=[O:38])[NH:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:8]3[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=4)=[C:11]4[S:12][CH2:13][CH2:14][CH2:15][N:10]4[N:9]=3)[CH:17]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 674228643-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine

Product 1

HCID 58477096[3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-carbamic acid phenyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(3-Pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenylamine (prepared as described in Example 3) (30 mg, 0.097 mmol) was dissolved in dry DCM (1 mL) under nitrogen atmosphere. Triethylamine (0.018 mL, 0.126 mmol, 1.3 eq) and phenylchloroformate (0.015 mL, 0.117 mmol, 1.2 eq) were added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with DCM and washed with water, dried over Na2SO4 and concentrated to dryness. The residue was taken up with ethylether and filtered to give 27 mg (65%) of [3-(3-pyridin-4-yl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]thiazin-2-yl)-phenyl]-carbamic acid phenyl ester as white solid.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. filtrationfiltered

Sources & evidence

ORD record
ord-dfefe41c60d2428fb82076a9873aaae8
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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