Citric Acid → HCID 86710845, compound

HRID 1471803Notes

Reaction equation

HRID 1471803 reaction equation
[CH3:1][N:2]([CH2:4]/[CH:5]=[CH:6]/[C:7]([NH:9][C:10]1[CH:11]=[C:12]2[C:25]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([F:34])=[C:31]([Cl:33])[CH:32]=3)=[N:24][CH:23]=[N:22][C:13]2=[CH:14][C:15]=1[O:16][C@@H:17]1[CH2:21][O:20][CH2:19][CH2:18]1)=[O:8])[CH3:3].[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38]>C(O)C>[CH3:1][N:2]([CH2:4]/[CH:5]=[CH:6]/[C:7]([NH:9][C:10]1[CH:11]=[C:12]2[C:25]([NH:26][C:27]3[CH:28]=[CH:29][C:30]([F:34])=[C:31]([Cl:33])[CH:32]=3)=[N:24][CH:23]=[N:22][C:13]2=[CH:14][C:15]=1[O:16][C@@H:17]1[CH2:21][O:20][CH2:19][CH2:18]1)=[O:8])[CH3:3].[C:35]([O-:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([O-:45])=[O:44])([C:39]([O-:41])=[O:40])[OH:38]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 10184653Afatinib

Product 1

HCID 86710845HCID 86710845, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Ethanol (2 ml) was added to 100 mg (0.205 mmol) afatinib free base and the light yellow solution was stirred at room temperature. A solution of 39.4 mg (0.205 mmol) citric acid in 0.5 ml ethanol was added over the course of 2 min. Another 0.5 ml ethanol was added. Precipitation was observed and the mixture was stirred for 15 min. The solid was filtered, washed with 0.5 ml ethanol and dried on rotary evaporator at 50° C. for 2 h to give 80 mg (57%) of a light yellow solid.

Workup

  1. customPrecipitation
  2. stirringthe mixture was stirred for 15 min
  3. filtrationThe solid was filtered
  4. washwashed with 0.5 ml ethanol
  5. customdried on rotary evaporator at 50° C. for 2 h

Sources & evidence

ORD record
ord-951dc02bc7024171a7e52e9c01243158
Source dataset
uspto-grants-2015_04
Patent number
US09012464B2

Reaction notes

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