Dicyclohexylcarbodiimide → 2-[6-(4-Cyanophenyl)-5-(cyclopropylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]-N-[(4-cyanophenyl)sulfonyl]acetamide

HRID 421802

Reaction equation

HRID 421802 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16](O)=[O:17])[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11]([CH3:30])=[C:10]2[C:31]([CH:33]2[CH2:35][CH2:34]2)=[O:32])=[CH:5][CH:4]=1)#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:51]([C:53]1[CH:58]=[CH:57][C:56]([S:59]([NH2:62])(=[O:61])=[O:60])=[CH:55][CH:54]=1)#[N:52]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]([NH:62][S:59]([C:56]3[CH:55]=[CH:54][C:53]([C:51]#[N:52])=[CH:58][CH:57]=3)(=[O:60])=[O:61])=[O:17])[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:27])[F:29])[CH:21]=3)[C:11]([CH3:30])=[C:10]2[C:31]([CH:33]2[CH2:35][CH2:34]2)=[O:32])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 76566p-CyanobenzenesulphonamideHCID 59684871[6-(4-Cyanophenyl)-5-(cyclopropylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetic acid

Product 1

HCID 596848492-[6-(4-Cyanophenyl)-5-(cyclopropylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]-N-[(4-cyanophenyl)sulfonyl]acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [6-(4-cyanophenyl)-5-(cyclopropylcarbonyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetic acid (Example 31) (100 mg, 0.21 mmol), 1,3-dicyclohexylcarbodiimide (41.5 mg, 0.23 mmol), 4-cyanobenzene-1-sulfonamide (41.5 mg, 0.23 mmol) and 4-dimethylaminopyridine (28 mg, 0.23 mmol) in dichloromethane (4 ml) is stirred for 48 hours. The product is extracted with dichloromethane, washed with 2 N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water 10:90→90:10).

Workup

  1. extractionThe product is extracted with dichloromethane
  2. washwashed with 2 N hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water 10:90→90:10)

Sources & evidence

ORD record
ord-bd567958cfad427da91267de19faf5a2
Source dataset
uspto-grants-2012_01
Patent number
US08101615B2

Linked notes

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