Phenylboronic Acid → N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-phenylpyrimidin-4-yloxy)-cyclopentane-carboxamide

HRID 1429157Notes

Reaction equation

HRID 1429157 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26](Cl)[N:25]=4)[CH2:20][CH:19]3[C:31]([N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH3:34])=[O:32])=[O:17])[CH2:12][CH:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:41]1(B(O)O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([S:4]([NH:7][C:8]([C:10]2([NH:15][C:16]([CH:18]3[CH2:22][CH:21]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[N:25]=4)[CH2:20][CH:19]3[C:31]([N:33]([CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[CH3:34])=[O:32])=[O:17])[CH2:12][CH:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 72253694N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-chloropyrimidin-4-yloxy)-cyclopentane-carboxamide

Product 1

HCID 68590067N-(1-Cyclopropanesulfonylaminocarbonyl-2-vinyl-cyclopropyl)-2-(hex-5-enyl-methyl-amino-carbonyl)-4-(2-phenylpyrimidin-4-yloxy)-cyclopentane-carboxamideYield 13%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

Compound 10f (43 mg, 72.4 mmol), phenylboronic acid (13 mg, 109 μmol) and (PPh3)2PdCl2 (5 mg, 7.2 umol) were mixed in a microwave reaction vial and heated in the microwave at 120° C. for 20 min. The reaction mixture was then quenched by addition of citric acid (20 ml) and extracted 2 times with DCM (10 ml). The combined organic phases were washed with water (2×10 ml) and brine (10 ml), dried over MgSO4 and filtered. The solvent was removed in vacuo and the crude product was purified by preparative LC-MS which gave the title compound (5.9 mg, 13%), (ESI+)=636 (MH+).

Workup

  1. customThe reaction mixture was then quenched by addition of citric acid (20 ml)
  2. extractionextracted 2 times with DCM (10 ml)
  3. washThe combined organic phases were washed with water (2×10 ml) and brine (10 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe crude product was purified by preparative LC-MS which

Sources & evidence

ORD record
ord-58abb5d09a6b429bbf883dc5469be8fa
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

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