Toluene → HCID 57886961, compound

HRID 1819322Notes

Reaction equation

HRID 1819322 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].C(=O)([O-])[O-].[K+].[K+].[NH2:11][C:12]1[C:16]([C:17]#[N:18])=[C:15]([N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:20]2)[N:14]([CH2:33][C:34]2[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=2[Cl:41])[C:13]=1[C:42]([O:44]CC)=O.C1(C)C=CC=CC=1>N1C=CC=CC=1>[Cl:41][C:35]1[CH:36]=[CH:37][C:38]([F:40])=[CH:39][C:34]=1[CH2:33][N:14]1[C:13]2[C:42](=[O:44])[N:2]([CH3:1])[C:3](=[S:4])[NH:11][C:12]=2[C:16]([C:17]#[N:18])=[C:15]1[N:19]1[CH2:24][CH2:23][CH2:22][C@@H:21]([NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:20]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 11167Methyl isothiocyanateHCID 11430Potassium CarbonateHCID 57886960HCID 57886960, compound

Product 1

HCID 57886961HCID 57886961, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

Methyl isothiocyanate (7.36 ml) and potassium carbonate (14.86 g) were added to a solution (200 ml) of ethyl 3-amino-5-{(3R)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-1-(2-chloro-5-fluorobenzyl)-4-cyano-1H-pyrrole-2-carboxylate (27.96 g) in pyridine, and the resulting mixture was stirred with heating at 130° C. for 13 hours. After the reaction solution was cooled to 25° C., toluene (50 ml) was added thereto and the resulting mixture was concentrated under reduced pressure. This procedure was repeated three times. The resulting residue was adjusted to pH 2 with an aqueous potassium hydrogensulfate solution and the solid precipitated was collected by filtration and washed with water and then hexane. The solid thus obtained was dried at 45° C. under reduced pressure to obtain the title compound (28.56 g).

Workup

  1. temperatureAfter the reaction solution was cooled to 25° C.
  2. concentrationthe resulting mixture was concentrated under reduced pressure
  3. customthe solid precipitated
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customThe solid thus obtained
  7. customwas dried at 45° C. under reduced pressure

Sources & evidence

ORD record
ord-efb30c2bf5934c22a917ed2c4c0757b5
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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