Water → HCID 22260271, compound

HRID 2186718Notes

Reaction equation

HRID 2186718 reaction equation
[CH3:1][C:2]1([CH3:22])[C:7]2[CH:8]=[C:9]([C:12]3[N:16]([CH3:17])[C:15]([C:18]#[N:19])=[CH:14][C:13]=3[CH3:20])[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:21])[O:3]1.[Br:23]N1C(=O)CCC1=O.N1C=CC=CC=1.O>C1COCC1>[CH3:1][C:2]1([CH3:22])[C:7]2[CH:8]=[C:9]([C:12]3[N:16]([CH3:17])[C:15]([C:18]#[N:19])=[C:14]([Br:23])[C:13]=3[CH3:20])[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:21])[O:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 67184N-bromobutanimideHCID 22260270HCID 22260270, compound

Product 1

HCID 22260271HCID 22260271, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1,4-dimethyl-1H-pyrrole-2-carbonitrile (1 eq, 0.15 g, 0.51 mmol) in THF (5 mL) at −78° C. was added N-bromosuccinimide (1.1 eq, 0.1 g, 0.56 mmol). The solution was allowed to warm and stir for 16 hours. Pyridine (1 mL) was added and the mixture was poured into water (15 mL), the layers were separated, the aqueous layer was extracted with ethyl acetate (3×10 mL) and the combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The product, 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-3-bromo-1,4-dimethyl-1 H-pyrrole-2-carbonitrile was obtained by crystallization from 20% ethyl acetate/hexane as a white crystalline solid. 1H NMR (300 MHZ, d6-DMSO) δ1.64 (s, 6H), 1.93 (s, 3H), 3.57 (s, 3H), 7.01 (d, 1H, J=8 Hz), 7.31 (dd, 1H, J=1.95, 8 Hz), 7.35 (s, 1H), 10.43 (s, 1H). MS m/z (ESI (−)) 372/374 (M−H)−. Anal. calcd for C17H16N3O2, C, 54.6; H, 4.31; N, 11.2. Found: C, 54.8; H, 4.42; N, 11.1.

Workup

  1. temperatureto warm
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c27bbd7f389441c39e354318645c1a6d
Source dataset
uspto-grants-2002_06
Patent number
US06407101B1

Reaction notes

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