Isopropyl chloroformate → {2-dimethylcarbamoyl-6-fluoro-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-carbamic Acid Isopropyl Ester

HRID 2234642Notes

Reaction equation

HRID 2234642 reaction equation
[NH2:1][C:2]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][N:20]([S:31]([C:34]4[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=4)(=[O:33])=[O:32])[C:17]3=[N:18][CH:19]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C(=O)(O)[O-].[Na+].Cl[C:47]([O:49][CH:50]([CH3:52])[CH3:51])=[O:48]>ClCCl.C1(C)C=CC=CC=1>[CH:50]([O:49][C:47](=[O:48])[NH:1][C:2]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][N:20]([S:31]([C:34]4[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=4)(=[O:32])=[O:33])[C:17]3=[N:18][CH:19]=2)=[CH:9][C:3]=1[C:4](=[O:5])[N:6]([CH3:8])[CH3:7])([CH3:52])[CH3:51]

Participants

6

Reactant 3

HCID 7917Isopropyl chloroformateHCID 516892Sodium BicarbonateHCID 577314782-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide

Product 1

HCID 57731657{2-dimethylcarbamoyl-6-fluoro-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-carbamic Acid Isopropyl Ester

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

45 mg (0.08 mmol) of 2-amino-3-fluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 1.0 mL dichloromethane and 1.0 mL of a saturated aqueous solution of sodium bicarbonate was added. The biphasic solution was cooled to 0° C. in an ice bath and, while stirring vigorously, 161 μL (0.161 mmol) of 1 M isopropyl chloroformate in toluene was added. The reaction was allowed to stir in the ice bath and allowed to warm to room temperature overnight (16 hours). The layers were separated and the organic layer was washed twice with water. The organic layer was then dried over sodium sulfate and concentrated. MS: m/z 645.1 (M+H+).

Workup

  1. temperatureto warm to room temperature overnight (16 hours)
  2. customThe layers were separated
  3. washthe organic layer was washed twice with water
  4. dry with materialThe organic layer was then dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-11c7e7ee481941e38d71d2016c055c52
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

Loading…