Hydrochloric Acid → HCID 15219370, compound

HRID 1707937Notes

Reaction equation

HRID 1707937 reaction equation
[O:1]=[C:2]1[C:7]2=[C:8]([S:15]([NH2:18])(=[O:17])=[O:16])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][O:3]1.[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([NH:29][C:30](=O)[O:31]C2C=CC=CC=2)[N:22]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.O>[CH3:28][O:27][C:25]1[CH:26]=[C:21]([O:20][CH3:19])[N:22]=[C:23]([NH:29][C:30]([NH:18][S:15]([C:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]3[CH2:5][CH2:4][O:3][C:2](=[O:1])[C:7]=23)(=[O:17])=[O:16])=[O:31])[N:24]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 18960415HCID 18960415, compound

Product 1

HCID 15219370HCID 15219370, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A 60 mg (0.23 mmol) sample of 3,4-dihydro-1-oxo-1H-[1,4]oxazino[4,3-a]indole-10-sulfonamide was dissolved in 1 mL dry acetonitrile and 70 mg (0.27 mmol) of phenyl (4,6-dimethoxypyrimidin-2-yl)carbamate was added. To this was added 0.040 mL of DBU and the mixture was stirred at room temperature for 30 minutes. A 0.2N solution of HCl was then added until the pH of the mixture was less than 2. Additional water was added and the resulting precipitate was collected by filtration and rinsed with water, then ethyl ether to afford 70 mg of the title compound, m.p. 206°-210° C. dec.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washrinsed with water

Sources & evidence

ORD record
ord-e0d0aad48c9643518032dbe38a97e001
Source dataset
uspto-grants-1994_10
Patent number
US05356862

Reaction notes

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