Sodium Carbonate → HCID 178481875, compound

HRID 1915930Notes

Reaction equation

HRID 1915930 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[N:29]=[C:30](Br)[S:31][C:32]=2[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:50]2[N:55]=[C:54]([OH:56])[CH:53]=[CH:52][CH:51]=2)O1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][CH2:16][N:15]([C:19]2[N:23]([CH3:24])[N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[N:29]=[C:30]([C:50]3[CH:51]=[CH:52][CH:53]=[C:54]([OH:56])[N:55]=3)[S:31][C:32]=2[NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:27])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 86680129tert-butyl N-[4-[[5-[(4S)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-bromo-thiazol-5-yl]carbamateHCID 178431067HCID 178431067, compound

Product 1

HCID 178481875HCID 178481875, compound

Reagents, catalysts & solvents 2

HCID 178477754HCID 178477754, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

In a microwave reaction vial, tert-butyl N-[4-[[5-[(4S)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-bromo-thiazol-5-yl]carbamate (200 mg, 0.31 mmol), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ol (205 mg, 0.93 mmol) and PDCL2(DPPF) (23 mg, 0.031 mmol) were dissolved in acetonitrile (8 mL). Potassium acetate (1.0M, 0.46 mL, 0.46 mmol) was sodium carbonate (1.0M, 0.46 mL, 0.46 mmol) were added and the mixture was irradiated with a microwave for 30 min at 120° C. The mixture was cooled, filtered through Na2SO4 and Celite, concentrated and purified via flash chromatography, methanol/DCM 0% to 10% to afford tert-butyl N-[4-[[5-[(4S)-4-(benzyloxycarbonylamino)azepan-1-yl]-1-methyl-pyrazol-4-yl]carbamoyl]-2-(6-hydroxy-2-pyridyl)thiazol-5-yl]carbamate.

Workup

  1. customIn a microwave reaction vial
  2. additionwere added
  3. customthe mixture was irradiated with a microwave for 30 min at 120° C
  4. temperatureThe mixture was cooled
  5. filtrationfiltered through Na2SO4 and Celite
  6. concentrationconcentrated
  7. custompurified via flash chromatography, methanol/DCM 0% to 10%

Sources & evidence

ORD record
ord-f1a24242ccf143a9a173eaae239072fa
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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