5-Tert-butylpyridin-2-amine → HCID 86699118, compound

HRID 1424204Notes

Reaction equation

HRID 1424204 reaction equation
Br[CH2:2][C:3]([C@H:5]1[N:8]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C:7](=[O:16])[C@@H:6]1[CH3:17])=O.[C:18]([C:22]1[CH:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=1)([CH3:21])([CH3:20])[CH3:19]>C(#N)C>[C:18]([C:22]1[CH:23]=[CH:24][C:25]2[N:26]([CH:2]=[C:3]([C@H:5]3[N:8]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C:7](=[O:16])[C@@H:6]3[CH3:17])[N:28]=2)[CH:27]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 205879625-Tert-butylpyridin-2-amineHCID 86699119HCID 86699119, compound

Product 1

HCID 86699118HCID 86699118, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3R,4S)-4-(2-bromoacetyl)-1-(tert-butyldimethylsilyl)-3-methylazetidin-2-one (Preparation 72, 1144 mg, 3.57 mmol) and 5-(tert-butyl)pyridin-2-amine (537 mg, 3.57 mmol) were mixed in acetonitrile (10 mL) and the reaction mixture stirred for 18 hours at room temperature, then an additional 18 hours at 65° C. to complete the dehydration. The reaction solvent was removed in vacuo and the residue was purified by silica gel column chromatography eluting with 0-100% ethyl acetate in hexanes to afford the title compound which was immediately taken to the next step.

Workup

  1. customan additional 18 hours
  2. customat 65° C.
  3. customThe reaction solvent was removed in vacuo
  4. customthe residue was purified by silica gel column chromatography
  5. washeluting with 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-69e5e4cc1d25493f986786f957a1f80b
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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