Sodium Bicarbonate → HCID 22637162, compound

HRID 2416081Notes

Reaction equation

HRID 2416081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH2:28]C)=[C:17]([NH:20][C:21](=[O:26])[CH:22]=[CH:23][CH2:24]Br)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:30]#[N:31])[CH:5]=[CH:6][C:7]=1[F:8].[NH:32]1[CH2:36][CH2:35][C@@H:34]([OH:37])[CH2:33]1.[C:38](=[O:41])(O)[O-].[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:27][CH3:28])=[C:17]([NH:20][C:21](=[O:26])[CH2:22][CH:23]([N:9]4[CH2:4][CH2:3][CH:38]([OH:41])[CH2:10]4)[CH2:24][N:32]4[CH2:36][CH2:35][CH:34]([OH:37])[CH2:33]4)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:30]#[N:31])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2759337(R)-3-PyrrolidinolHCID 69464668HCID 69464668, compound

Product 1

HCID 22637162HCID 22637162, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[4-(3-Chloro-4-fluoro-phenylamino)-3-cyano-7-ethoxy-6-quinolinyl)-4-bromo-2-butenamide (150 mg, 0.3 mmol) in 0.7 mL of DMF was reacted with (R)-(+)-3-pyrrolidinol (0.2 mL, 2.4 mmol) at room temperature. After reacting for 4 hours, the reaction solution was added into saturated sodium bicarbonate solution. The resulting precipitate was filtered and washed with water and ether consecutively to give 150 mg of the title compound as a light brown solid, mp 139-143° C.; MS (ES) m/z calcd. 583.2236, found 583.2242 (M+1).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water and ether consecutively

Sources & evidence

ORD record
ord-6b047848f1054497b7d3283349c9cf7a
Source dataset
uspto-grants-2004_11
Patent number
US06821988B2

Reaction notes

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