Water → HCID 57504292, compound

HRID 1097983Notes

Reaction equation

HRID 1097983 reaction equation
Br[CH:2]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([CH3:11])[N:10]=1)=[O:4].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[C:30]2=[N:31][CH:32]=[N:33][C:34]([SH:35])=[C:29]2[CH:28]=[N:27]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[C:30]2=[N:31][CH:32]=[N:33][C:34]([S:35][CH:2]([CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH3:18])[C:3]([NH:5][C:6]3[S:7][CH:8]=[C:9]([CH3:11])[N:10]=3)=[O:4])=[C:29]2[CH:28]=[N:27]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 57504475HCID 57504475, compoundHCID 178527883HCID 178527883, compound

Product 1

HCID 57504292HCID 57504292, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-4-(2-methoxyethoxy)-N-(4-methyl-1,3-thiazol-2-yl)butanamide (104 mg, 0.308 mmol) in DMF (1 mL) was added to a stirred solution of 1-(2-chlorophenyl)-1H-pyrazolo[3,4-d]pyrimidine-4-thiol (81.0 mg, 0.308 mmol) and K2CO3 (51.1 mg, 0.370 mmol) in DMF (2 mL). The reaction mixture was kept at ambient temperature for 3 hrs (45° C. and 17 hrs for example 54, 55 and 56). Water and EtOAc were added, and the two phases were separated. The aqueous phase was extracted with EtOAc. The organic extracts were combined and washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:1/1) to give the title compound as a colourless viscous oil (145 mg), 1H NMR (300 MHz, CDCl3) δ 11.06 (br s, 1H), 8.93 (s, 1H), 8.30 (s, 1H), 7.62 (m, 1H), 7.49 (m, 3H), 6.51 (s, 1H), 5.14 (t, 1H), 3.77 (m, 1H), 3.67 (m, 1H), 3.59 (m, 2H), 3.50 (m, 2H), 3.33 (s, 3H), 2.60 (m, 1H), 2.27 (m, 4H), HRMS: calcd for (M+H+) C22H2435ClN6O3S2: 518.1040. Found: 519.1050.

Workup

  1. custom(45° C. and 17 hrs for example 54, 55 and 56)
  2. customthe two phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:1/1)

Sources & evidence

ORD record
ord-09cfe1d938b04ac7b9cb140f6f467e9b
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

Loading…