Dimethylcarbamoyl Chloride → HCID 68971603, compound

HRID 657567Notes

Reaction equation

HRID 657567 reaction equation
[CH3:1][O:2][C:3]1[C:29]([O:30][CH3:31])=[CH:28][C:6]2[CH2:7][CH2:8][N:9]([C:12](=[O:27])[CH2:13][CH2:14][N:15]([CH2:17][CH:18]3[CH2:25][C:24]4[C:19]3=[CH:20][CH:21]=[C:22]([OH:26])[CH:23]=4)[CH3:16])[CH2:10][CH2:11][C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH3:39][N:40]([CH3:44])[C:41]([Cl:43])=[O:42]>N1C=CC=CC=1>[ClH:43].[CH3:39][N:40]([CH3:44])[C:41](=[O:42])[O:26][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH:18]([CH2:17][N:15]([CH2:14][CH2:13][C:12]([N:9]1[CH2:10][CH2:11][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:29]([O:30][CH3:31])=[CH:28][C:6]=3[CH2:7][CH2:8]1)=[O:27])[CH3:16])[CH2:25]2

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 68531949HCID 68531949, compound

Product 1

HCID 68971603HCID 68971603, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At ambient temperature, to 0.7 g (1.65 mmol) of the compound of Example 43 in 5 ml of pyridine, there are added, all at once, 0.3 mL (2.06 mmol/1.25 eq.) of triethylamine and then, dropwise, 0.2 mL (2.06 mmol/1.25 eq.) of dimethylcarbamoyl chloride. Stirring is carried out at ambient temperature overnight and the mixture is then concentrated. The residue is chromatographed over 130 g of silica (eluant: dichloromethane/ethanol/ammonia: 95/5/0.5) to yield the expected product in the form of the base. It is dissolved in 7 mL of ethanol and treated with 0.5 mL of 3N ethanolic HCl to yield the hydrochloride.

Workup

  1. concentrationthe mixture is then concentrated
  2. customThe residue is chromatographed over 130 g of silica (eluant: dichloromethane/ethanol/ammonia: 95/5/0.5)

Sources & evidence

ORD record
ord-a127309f123b4b608a956d0a7ce1a449
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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