Dimethylcarbamoyl Chloride → HCID 69508929, compound

HRID 1354056Notes

Reaction equation

HRID 1354056 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][C@@H:6]([NH:14][C:15]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])=[CH:19][N:18]=[C:17]([N:28]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH3:29])[N:16]=1)[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].CCN(CC)CC.[CH3:44][N:45]([CH3:49])[C:46](Cl)=[O:47]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][C@@H:6]([NH:14][C:15]1[C:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[F:27])=[CH:19][N:18]=[C:17]([N:28]([CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[CH3:29])[N:16]=1)[C:7]1[CH:12]=[CH:11][C:10]([O:13][C:46]([N:45]([CH3:49])[CH3:44])=[O:47])=[CH:9][CH:8]=1)[CH3:2]

Participants

7

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 69508751HCID 69508751, compound

Product 1

HCID 69508929HCID 69508929, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-3-(5-(2-fluorophenyl)-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-hydroxyphenyl)propanoic acid ethyl ester (1.0 eq), DMAP (1.0 eq), Et3N (1.2 eq) and dimethylcarbamyl chloride (1.2 eq) in CH2Cl2 was stirred at 22° C. for 8 hr. The mixture was diluted with EtOAc, and the resulting solution was washed successively with water, 0.5 M citric acid, sat. NaHCO3 and sat. NaCl. The CH2Cl2/EtOAc extracts were treated with MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel using 6:4 hexanes/EtOAc to give (R)-3-(5-(2-fluorophenyl)-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-(dimethylaminocarbonyl)oxyphenyl)propanoic acid ethyl ester.

Workup

  1. washthe resulting solution was washed successively with water, 0.5 M citric acid, sat. NaHCO3 and sat. NaCl
  2. additionThe CH2Cl2/EtOAc extracts were treated with MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel using 6:4 hexanes/EtOAc

Sources & evidence

ORD record
ord-33f0b1e0b79d4acea64004f2f3fd1bea
Source dataset
uspto-grants-2007_05
Patent number
US07223762B2

Reaction notes

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