Ammonium Hydroxide → HCID 68668726, compound

HRID 1914734Notes

Reaction equation

HRID 1914734 reaction equation
C([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33]1[N:42]=[CH:41][C:40]2[CH:39]=[CH:38][C:37]3[C:43]([C:47]([O:49]CC)=O)=[N:44][N:45]([CH3:46])[C:36]=3[C:35]=2[N:34]=1)=[O:24])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[NH4+:52].[OH-]>C(O)C>[NH:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33]1[N:42]=[CH:41][C:40]2[CH:39]=[CH:38][C:37]3[C:43]([C:47]([NH2:52])=[O:49])=[N:44][N:45]([CH3:46])[C:36]=3[C:35]=2[N:34]=1)=[O:24]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 68668438HCID 68668438, compound

Product 1

HCID 68668726HCID 68668726, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Ethyl 8-{2-[((S)—N-FMOC-pyrrolidine-2-carbonyl)-amino]-phenylamino}-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (200 mg, 0.29 mmol) was suspended in 20 mL of ethanol and 20 mL of NH4OH 30% mixture. The mixture was maintained at 65° C. under stirring for 12 h in a closed bottle. The solvent was then evaporated to dryness, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 94/6) to afford 60 mg (47% yield) of the title compound.

Workup

  1. customThe solvent was then evaporated to dryness
  2. dissolutionthe residue redissolved with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customThe crude product was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 94/6)

Sources & evidence

ORD record
ord-6369e7db9b164069bb7ba6cfa7983e55
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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