Water → HCID 58550825, compound

HRID 1907981Notes

Reaction equation

HRID 1907981 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]2[N:8]3[CH:26]=[CH:25][CH:24]=[C:9]3[C:10]3([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[O:11][C:6]=2[CH:5]=1)(=O)[NH2:2].N1C(Cl)=NC(Cl)=NC=1Cl.O>CN(C=O)C>[C:1]([C:4]1[CH:28]=[CH:27][C:7]2[N:8]3[CH:26]=[CH:25][CH:24]=[C:9]3[C:10]3([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[O:11][C:6]=2[CH:5]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 58551319HCID 58551319, compound

Product 1

HCID 58550825HCID 58550825, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 7′-carbamoylspiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate (2.7 g, 7.1 mmol) and cyanuric chloride (1.3 g, 7.1 mmol) in DMF (10 mL) was stirred at room temperature for 1 hour. The reaction was poured into water and the product was extracted into ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to yield a crude mixture that was purified by silica gel chromatography eluting with 0-100% EtOAc in Hexanes. Pure fractions were combined and concentrated to yield tert-butyl 7-cyanospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-carboxylate (1.1 g, 44%). ESI-MS m/z calc. 365.4. found 366.3 (M+1)+. Retention time: 2.00 minutes (3 min run).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto yield a crude mixture that
  6. customwas purified by silica gel chromatography
  7. washeluting with 0-100% EtOAc in Hexanes
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-12ee0c2044f440e4bb75f1241c98c3a4
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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