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

HRID 1366259Notes

Reaction equation

HRID 1366259 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]([CH2:15][C:16]([OH:18])=O)[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]([C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)=[O:32])=[CH:5][CH:4]=1)#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:53]([C:55]1[CH:60]=[CH:59][C:58]([S:61]([NH2:64])(=[O:63])=[O:62])=[CH:57][CH:56]=1)#[N:54]>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:64][S:61]([C:58]3[CH:57]=[CH:56][C:55]([C:53]#[N:54])=[CH:60][CH:59]=3)(=[O:62])=[O:63])=[O:18])[C:13](=[O:19])[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=3)[C:11]([CH3:30])=[C:10]2[C:31]([C:33]2[O:34][CH:35]=[CH:36][CH:37]=2)=[O:32])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 76566p-CyanobenzenesulphonamideHCID 59411320[6-(4-Cyanophenyl)-5-(2-furoyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetic acid

Product 1

HCID 594112942-[6-(4-Cyanophenyl)-5-(2-furoyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydro-pyrimidin-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-(2-furoyl)-4-methyl-2-oxo-3-[3-(trifluoromethyl)phenyl]-3,6-dihydropyrimidin-1(2H)-yl]acetic acid (Example 29A) (75 mg, 0.14 mmol), 1,3-dicyclohexylcarbodiimide (33 mg, 0.16 mmol), 4-cyanobenzene-1-sulfonamide (30 mg, 0.16 mmol) and 4-dimethylaminopyridine (20 mg, 0.16 mol) 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-4aebbe793791452ab5314ac2151d9809
Source dataset
uspto-grants-2011_02
Patent number
US07893073B2

Reaction notes

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