Dicyclohexylcarbodiimide → HCID 131730567, compound

HRID 2090521Notes

Reaction equation

HRID 2090521 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:9]1[O:10][CH2:11][C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[CH:13]=[C:8]1[CH:7]=[C:6]2[C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([OH:48])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1.[F:49][C:50]1[CH:58]=[C:57]([F:59])[CH:56]=[CH:55][C:51]=1[C:52](O)=[O:53].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:31](=[CH:32][C:33]=1[O:34][CH3:35])[CH:9]1[O:10][CH2:11][C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:18][CH:19]=3)[CH:13]=[C:8]1[CH:7]=[C:6]2[C:36]1[CH:37]=[CH:38][C:39]([C:42]2[CH:47]=[CH:46][C:45]([O:48][C:52](=[O:53])[C:51]3[CH:55]=[CH:56][C:57]([F:59])=[CH:58][C:50]=3[F:49])=[CH:44][CH:43]=2)=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 741022,4-Difluorobenzoic acidHCID 131730568HCID 131730568, compound

Product 1

HCID 131730567HCID 131730567, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 8,9-dimethoxy-6-[4′-hydroxybiphen-4-yl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[1,2-b]pyran (0.95 g, 0.5 mmol) and 2,4-difluorobenzoic acid (0.09 g, 0.5 mmol) in DCM (40 mL) containing 4-dimethylaminopyridine (0.01 g) and N,N′-dicyclohexylcarbodiimide (0.11 g, 1.6 mmol) under N2 was stirred at room temperature for 2 h. The resulting mixture was filtered through a short plug of silica using DCM as eluent. The solvent was removed under reduced pressure and the residue chromatographed on silica using EtOAc (0-20% gradient in toluene) as eluent. The solvent was removed under reduced pressure and the residue washed with acetone to give the title compound (0.29 g, 70%) as a pale violet powder, mp 249-250° C.

Workup

  1. filtrationThe resulting mixture was filtered through a short plug of silica
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed on silica
  4. customThe solvent was removed under reduced pressure
  5. washthe residue washed with acetone

Sources & evidence

ORD record
ord-e9bf5cda9bc047efa9d024c6650c0205
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

Loading…