Toluene → HCID 59463481, compound

HRID 1712988Notes

Reaction equation

HRID 1712988 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([C:30](=[O:42])[NH:31][C:32]3[S:33][C:34]4[C:39]([N:40]=3)=[CH:38][CH:37]=[C:36](Br)[N:35]=4)[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[NH:49]1[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1.C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(O)(C)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([C:30](=[O:42])[NH:31][C:32]3[S:33][C:34]4[C:39]([N:40]=3)=[CH:38][CH:37]=[C:36]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)[N:35]=4)[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 59463480HCID 59463480, compound

Product 1

HCID 59463481HCID 59463481, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6386tert-ButanolSolvent

Conditions

Temperature
160 °C

Procedure

To title compound F, 4-{4-[1-(5-Bromo-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-2-cyclopentyl-ethyl]-benzenesulfonyl}-piperazine-1-carboxylic acid tert-butyl ester (0.1 g, 0.148 mmol) in a microwave vial was added Pd2 dba3 (0.013 g, 0.0148 mmol), Xanphos (0.011 g, 0.0295 mmol), sodium t-butoxide (0.028 g, 0.295 mmol), morpholine (0.019 g, 0.222 mmol), 2 mL toluene and 1 mL t-butanol. The sealed container was heated to 160° C. for 5 minutes in a microwave reactor. Workup entailed quenching into water and extraction with ethyl acetate. The combined organic layer was dried over MgSO4, filtered and evaporated to afford a yellow oil. Purification on silica (EtOAc/hexane) afforded the product as an oil. 1H NMR (400 MHz, CDCl3) δ 1.12 (m, 2H) 1.39 (s, 9H) 1.48 (m, 2H) 1.62 (m, 3H) 1.73 (m, 2H) 1.90 (m, 1H) 2.24 (m, 1H) 3.01 (s, 4H) 3.51 (s, 4H) 3.54-3.58 (m, 4H) 3.65 (m, 1H) 3.80-3.87 (m, 4H) 6.73 (s, 1H) 7.50 (d, J=8.34 Hz, 2H) 7.73 (d, J=8.08 Hz, 3H) MS 685.3 [M+1]+.

Workup

  1. customWorkup entailed quenching into water and extraction with ethyl acetate
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto afford a yellow oil
  6. customPurification on silica (EtOAc/hexane)

Sources & evidence

ORD record
ord-4c44d42d0e014534bee5336f466b61ae
Source dataset
uspto-grants-2010_09
Patent number
US07795257B2

Reaction notes

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