Water → HCID 11280075, compound

HRID 444735Notes

Reaction equation

HRID 444735 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:25]=[CH:24][C:16]2[NH:17][C:18](=[O:23])[O:19][C:20]([CH3:22])([CH3:21])[C:15]=2[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClS([N:30]=[C:31]=O)(=O)=O.CN(C=O)C.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:12]([C:31]#[N:30])=[CH:11][CH:10]=[C:9]1[C:13]1[CH:25]=[CH:24][C:16]2[NH:17][C:18](=[O:23])[O:19][C:20]([CH3:22])([CH3:21])[C:15]=2[CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 114392892-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-pyrrole-1-carboxylic acid tert-butyl ester

Product 1

HCID 11280075HCID 11280075, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-pyrrole-1-carboxylic acid tert-butyl ester (2.0 g, 5.8 mmol) in THF (anhydrous, 50 mL) at −78° C. was added chlorosulfonyl isocyanate (0.66 mL, 6.7 mmol). After 90 minutes, DMF (9 mL, 116 mmol) was added and the reaction was allowed to warm to room temperature. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layers were combined, washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash column chromatography on silica gel (30% ethyl acetate/hexane) gave 2-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-5-cyano-pyrrole-1-carboxylic acid tert-butyl ester (1.1 g, 52%) as a white powder, mp 165-167° C.; 1H NMR (d6-DMSO, 300 MHz): δ 1.36 (s, 9H), 1.61 (s, 6H), 6.44 (d, 1H, J=3.7 Hz), 6.92 (d, 1H, J=8.2 Hz), 7.27-7.32 (m, 2H), 7.36 (‘d’, 1H, J=1.5 Hz), 10.36 (s, 1H). MS (EI) m/z 367 [M]+.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via flash column chromatography on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ab39953d41e54d9ebbf65321f0b191d2
Source dataset
uspto-grants-2013_07
Patent number
US08476262B2

Reaction notes

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