Sodium Carbonate → 5-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-[3-(Methylsulfonyl)Phenyl]-4,5,6,7-Tetrahydro[1,3]Thiazolo[5,4-C]Pyridine

HRID 1713154Notes

Reaction equation

HRID 1713154 reaction equation
Br[C:2]1[S:3][C:4]2[CH2:5][N:6]([CH2:11][C:12]([N:14]3[CH2:19][CH2:18][N:17]([CH:20]4[CH2:23][CH2:22][CH2:21]4)[CH2:16][CH2:15]3)=[O:13])[CH2:7][CH2:8][C:9]=2[N:10]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:20]1([N:17]2[CH2:18][CH2:19][N:14]([C:12](=[O:13])[CH2:11][N:6]3[CH2:7][CH2:8][C:9]4[N:10]=[C:2]([C:32]5[CH:31]=[CH:30][CH:29]=[C:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:33]=5)[S:3][C:4]=4[CH2:5]3)[CH2:15][CH2:16]2)[CH2:23][CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 574205862-Bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine

Product 1

HCID 574206265-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-2-[3-(Methylsulfonyl)Phenyl]-4,5,6,7-Tetrahydro[1,3]Thiazolo[5,4-C]Pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine (40 mg, 0.1 mmol), 3-methylsulfonyl-phenylboronic acid (40 mg, 0.2 mmol), Na2CO3 (42 mg, 0.4 mmol) and Pd(PPh3)4 (12 mg, 0.01 mmol) in DME (4 mL) and water (1 mL) is degassed with argon and heated at 110° C. in a sealed tube overnight. The mixture is cooled and the layers are separated. The aqueous layer is extracted with EtOAc (4 ml) and the combined extracts are dried and evaporated. The residue is purified by PTLC to give the title compound as a white solid. MS (M+1): 475.0; 1H NMR (δ, CDCl3): 8.44 (t, 1H), 8.15 (td, 1H), 7.94 (td, 1H), 7.62 (t, 1H), 3.86 (s, 2H), 3.65 (q, 4H), 3.46 (d, 2H), 3.09 (s, 2H), 2.97 (s, 3H), 2.68-2.78 (m, 1H), 2.33 (q, 4H), 1.62-2.07 (m, 6H).

Workup

  1. customis degassed with argon
  2. temperatureThe mixture is cooled
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc (4 ml)
  5. customthe combined extracts are dried
  6. customevaporated
  7. customThe residue is purified by PTLC

Sources & evidence

ORD record
ord-390a2a4708d147d088841cf2f40a21c5
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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