Sodium Bicarbonate → HCID 11466063, compound

HRID 353132Notes

Reaction equation

HRID 353132 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[C:32]4[C:27](=[CH:28][C:29]([NH:36][CH2:37][CH3:38])=[C:30]([N+:33]([O-])=O)[CH:31]=4)[N:26]=[CH:25][N:24]=3)[CH2:19][CH2:18]2)=[O:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].[N:41]([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C(O)C.O.Cl.C(O)(=O)C.[C].[Pd]>[CH2:37]([N:36]1[C:29]2[C:30](=[CH:31][C:32]3[C:23]([N:20]4[CH2:21][CH2:22][N:17]([C:15]([NH:14][C:11]5[CH:12]=[CH:13][C:8]([O:1][C:2]6[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=6)=[CH:9][CH:10]=5)=[O:16])[CH2:18][CH2:19]4)=[N:24][CH:25]=[N:26][C:27]=3[CH:28]=2)[N:33]=[N:41]1)[CH3:38]

Participants

10

Reactant 4

HCID 516892Sodium BicarbonateHCID 11249274HCID 11249274, compound2×HCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compound

Product 1

HCID 11466063HCID 11466063, compoundYield 31.2%

Reagents, catalysts & solvents 5

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 394.8 mg (0.77 mmol) of N-(4-phenoxyphenyl)-4-(7-ethylamino-6-nitro-4-quinazolinyl)-1-piperazinecarboxamide (Compound 109) obtained in Example 109 in 8 ml of ethanol was added 60 mg of 10% palladium-carbon, followed by stirring for 7.5 hours in a stream of hydrogen. The catalyst was separated by filtration with Celite and the solvent was evaporated. The obtained residue was dissolved in a mixture of 10 ml of water, 1 ml of concentrated hydrochloric acid and 10 ml of acetic acid, and 106.2 mg (1.54 mmol) of sodium nitrite was added thereto under ice-cooling, followed by stirring at the same temperature for 4 hours. After the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate, the precipitated crystals were collected by filtration, washed with water, and dried, followed by purification by silica gel column chromatography to give 119.3 mg (0.24 mmol) of the desired compound as colorless crystals.

Workup

  1. customThe catalyst was separated by filtration with Celite
  2. customthe solvent was evaporated
  3. additionwas added
  4. temperatureunder ice-cooling
  5. filtrationthe precipitated crystals were collected by filtration
  6. washwashed with water
  7. customdried
  8. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-605d97adc0554c208b7746647278b527
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

Loading…