Sodium Nitrite → HCID 178452585, compound

HRID 1037363Notes

Reaction equation

HRID 1037363 reaction equation
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[C:22]([NH2:30])[C:23]([NH2:29])=[CH:24][CH:25]=4)[O:20][C:19]=3[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N:38]([O-])=O.[Na+]>C(O)(=O)C.O>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21]([O:20][C:19]=3[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[C:22]3[NH:30][N:38]=[N:29][C:23]3=[CH:24][CH:25]=4)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 23668193Sodium Nitrite2×HCID 67067961{1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 178452585HCID 178452585, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of {1-[4-(7,8-diamino-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (80 mg, 0.16 mmol) in glacial acetic acid (2 mL) and water (1 mL) at 0° C. was added NaNO2 (14 mg, 0.20 mmol). The resulting mixture was stirred at 0° C. for 30 mins, before allowing to warm to RT. After 16 hours, further NaNO2 (14 mg, 0.20 mmol) was added and the reaction mixture stirred at RT for a further 3 hours. The resultant mixture was poured onto water and the aqueous mixture was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with NaHCO3 (2×30 mL), brine, dried (NaSO4), filtered, and the solvent removed in vacuo to give the title compound as a brown solid (51 mg, 63%). LCMS (Method G): RT=3.76 min, [M+H]+=509.

Workup

  1. temperatureto warm to RT
  2. waitAfter 16 hours
  3. stirringthe reaction mixture stirred at RT for a further 3 hours
  4. extractionthe aqueous mixture was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed with NaHCO3 (2×30 mL), brine
  6. dry with materialdried (NaSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6ef124e2abfd4178996074d063e5e19f
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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