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Tert-butyl 4-(4-amino-3-methoxyphenyl)piperazine-1-carboxylate → 1-(4-(3-(Difluoromethoxy)-4-(5-fluoro-2-(2-methoxy-4-(piperazin-1-yl)phenylamino)pyrimidin-4-ylamino)phenyl)piperazin-1-yl)ethanone

HRID 1496973
Notes
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Reaction equation

HRID 1496973 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:24][CH:25]([F:27])[F:26])[C:5]([F:28])=[CH:4][N:3]=1.C(OC([N:36]1[CH2:41][CH2:40][N:39]([C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[C:44]([O:49][CH3:50])[CH:43]=2)[CH2:38][CH2:37]1)=O)(C)(C)C>C(OC(O)C)C.Cl>[F:26][CH:25]([F:27])[O:24][C:10]1[CH:11]=[C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]2)[CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[C:5]([F:28])=[CH:4][N:3]=[C:2]([NH:48][C:45]2[CH:46]=[CH:47][C:42]([N:39]3[CH2:38][CH2:37][NH:36][CH2:41][CH2:40]3)=[CH:43][C:44]=2[O:49][CH3:50])[N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 67128946Tert-butyl 4-(4-amino-3-methoxyphenyl)piperazine-1-carboxylateHCID 1181057451-(4-(4-(2-Chloro-5-fluoropyrimidine-4-ylamino)-3-(difluoromethoxy)phenyl)piperazin-1-yl)ethanone

Product 1

HCID 1181056391-(4-(3-(Difluoromethoxy)-4-(5-fluoro-2-(2-methoxy-4-(piperazin-1-yl)phenylamino)pyrimidin-4-ylamino)phenyl)piperazin-1-yl)ethanoneYield 22.2%

Reagents, catalysts & solvents 1

HCID 19698338
HCID 19698338, compound
Solvent

Conditions

Temperature
115 °C

Procedure

1-(4-(4-(2-chloro-5-fluoropyrimidine-4-ylamino)-3-(difluoromethoxy)phenyl)piperazin-1-yl)ethanone (320 mg) and tert-butyl-4-(4-amino-3-methoxyphenyl)piperazin-1-carboxylate (236 mg) were dissolved in 0.08M HCl ethoxyethanol solution (7.7 ml), and stirred at 115° C. overnight. Upon completion of the reaction, the mixture was distilled under reduced pressure to remove the solvent, and the thus obtained oil was diluted with ethyl acetate. The diluted mixture was neutralized with a saturated aqueous solution of sodium bicarbonate, subjected to layer separation, and the extracted organic layer obtained as a result of layer separation was dried with sodium sulfate. The dried organic layer was distilled under reduced pressure to remove the solvent and purified by column chromatography to obtain a target compound (100 mg, 22%).

Workup

  1. customUpon completion of the reaction
  2. distillationthe mixture was distilled under reduced pressure
  3. customto remove the solvent
  4. additionthe thus obtained oil was diluted with ethyl acetate
  5. customsubjected to layer separation
  6. customthe extracted organic layer obtained as
  7. customa result of layer separation
  8. dry with materialwas dried with sodium sulfate
  9. distillationThe dried organic layer was distilled under reduced pressure
  10. customto remove the solvent
  11. custompurified by column chromatography

Sources & evidence

ORD record
ord-bfb5a0a6b92b4cd3a52622bdb8003dec
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199944B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes