Water → 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)-N-(4-(piperidin-4-yl)thiazol-2-yl)pyridin-2-amine

HRID 1809592Notes

Reaction equation

HRID 1809592 reaction equation
[Br:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[O:4][C:5]1[C:6]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH:26]3[CH2:31][CH2:30][N:29](C([O-])=O)[CH2:28][CH2:27]3)[N:25]=2)=[N:7][CH:8]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:10]=1.C(O)(C(F)(F)F)=O.O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:3]=1[O:4][C:5]1[C:6]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[N:25]=2)=[N:7][CH:8]=[C:9]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 10340Sodium CarbonateHCID 866410944-(2-(3-(2-Bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)pyridin-2-ylamino)thiazol-4-yl)piperidine-1-carboxylate

Product 1

HCID 577426883-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)-N-(4-(piperidin-4-yl)thiazol-2-yl)pyridin-2-amineYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 20 mL vial was charged with tert-butyl. 4-(2-(3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)pyridin-2-ylamino)thiazol-4-yl)piperidine-1-carboxylate (100 mg, 0.145 mmol) and CH2Cl2 (2 mL). TFA (2 mL) was added and stirred at ambient temperature for 5 minutes. The reaction was poured into water and diluted with CH2Cl2. Solid Na2CO3 added slowly to neutralize the TFA. The reaction was extracted and dried to afford 3-(2-bromo-4-fluorophenoxy)-5-(3-methoxyphenylthio)-N-(4-(piperidin-4-yl)thiazol-2-yl)pyridin-2-amine (88 mg, 103% yield) as a yellow solid.

Workup

  1. additionA 20 mL vial was charged with tert-butyl
  2. extractionThe reaction was extracted
  3. customdried

Sources & evidence

ORD record
ord-d5b77da12f2e484bad93ee4bb1f1dfd7
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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