Dicyclohexylcarbodiimide → HCID 53361026, compound

HRID 1023369Notes

Reaction equation

HRID 1023369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:25]=[CH:26]/[C:27](O)=[O:28])[CH:5]=[C:6]([CH3:24])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:11][N:10]=1.[CH3:30][N:31]([CH3:54])[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][C:44]([CH2:47][N:48]3[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]3)=[CH:43][CH:42]=2)=[CH:34][CH:33]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:25]=[CH:26]/[C:27]([N:51]2[CH2:50][CH2:49][N:48]([CH2:47][C:44]3[CH:45]=[CH:46][C:41]([CH2:40][CH2:39][O:38][C:35]4[CH:34]=[CH:33][C:32]([N:31]([CH3:30])[CH3:54])=[CH:37][CH:36]=4)=[CH:42][CH:43]=3)[CH2:53][CH2:52]2)=[O:28])[CH:5]=[C:6]([CH3:24])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[CH:11][N:10]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 67327499HCID 67327499, compoundHCID 86673400HCID 86673400, compound

Product 1

HCID 53361026HCID 53361026, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a CH2Cl2 (5 mL) solution of (E)-3-[3-chloro-5-methyl-4-({5-[(4-methyl-benzyl)oxy]pyridin-2-yl}oxy)phenyl]prop-2-enoic acid (200 mg) was added N,N-dimethyl-4-{2-[4-(piperazin-1-ylmethyl)phenyl]ethoxy}aniline (191 mg), DCC (151 mg), and DMAP (5.96 mg) at room temperature, then the resultant mixture was stirred over night. The mixture was evaporated. The residue was added AcOEt, then filtered off, and the filtrate was evaporated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/0 and then AcOEt/MeOH=4/1) to afford (E)-3-[3-chloro-5-methyl-4-({5-[(4-methylbenzyl)oxy]-pyridin-2-yl}oxy)phenyl]-1-[4-(4-{2-[4-(dimethylamino)phenoxy]ethyl}benzyl)piperazin-1-yl]prop-2-en-1-one as a pale brown amorphous powder (184 mg).

Workup

  1. customThe mixture was evaporated
  2. additionThe residue was added AcOEt
  3. filtrationfiltered off
  4. customthe filtrate was evaporated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1 to 1/0

Sources & evidence

ORD record
ord-dd58bd8ad88d40bba04cc8211d4d4974
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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