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Acetonitrile → 1-(2-Bromothiazol-4-yl)-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

HRID 479701
Notes
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Reaction equation

HRID 479701 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5](C(O)=O)[N:6]=1.P(N=[N+]=[N-])([O:19][C:20]1C=CC=CC=1)(OC1C=CC=CC=1)=O.[N:29]1([CH2:35][C:36]2[N:41]=[C:40]([NH2:42])[CH:39]=[CH:38][CH:37]=2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.CC#[N:45]>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[C:5]([NH:45][C:20]([NH:42][C:40]2[CH:39]=[CH:38][CH:37]=[C:36]([CH2:35][N:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[N:41]=2)=[O:19])[N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 123414Diphenylphosphoryl azideHCID 27632092-Bromo-1,3-thiazole-4-carboxylic acidHCID 187716712-Amino-6-(piperidin-1-ylmethyl)pyridine

Product 1

HCID 187717461-(2-Bromothiazol-4-yl)-3-(6-piperidin-1-ylmethyl-pyridin-2-yl)urea

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
85 °C

Procedure

To a stirred suspension of 2-bromothiazole-4-carboxylic acid (5.13 g, 2 mmol) in anhydrous CH3CN (40 ml) at RT, under N2, TEA (3.80 ml, 27 mmol) and (PhO)2PON3 (5.90 ml, 27 mmol) were added. The resulting solution was heated to 85° C. Upon reaching 85° C., a solution of 6-(piperidylmethyl)-2-pyridylamine (4.74 g, 25 mmol) in anhydrous CH3CN (60 ml) was added. The reaction was maintained at this temperature for 2.25 h. After cooling to RT the mixture was diluted with CH2Cl2 (50 ml) then washed with a saturated solution of NH4Cl(aq) (40 ml). The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1/2:1/1:1, EtOAc:acetone) to yield the title compound as a pale yellow solid. MS m/z: 396 (M+H), 398 (M+3). Calc'd for C15H18BrN50S: 395.04.

Workup

  1. customUpon reaching 85° C.
  2. temperatureThe reaction was maintained at this temperature for 2.25 h
  3. temperatureAfter cooling to RT the mixture
  4. washthen washed with a saturated solution of NH4Cl(aq) (40 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on silica gel (3:1/2:1/1:1, EtOAc:acetone)

Sources & evidence

ORD record
ord-0a36fe690e6a48c58cd8470402f0ff46
Source dataset
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06645990B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes