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4-Methylmorpholine → 8-anilino-N-hydroxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 875117
Notes
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Reaction equation

HRID 875117 reaction equation
[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:22]([OH:24])=O)=[N:19][N:20]([CH3:21])[C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:25][N:26]1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.C1(C(NO)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:22]([NH:26][OH:25])=[O:24])=[N:19][N:20]([CH3:21])[C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11311898TriphenylmethylhydroxylamineHCID 441296031-methyl-8-(phenylamino)-4,5-dihydro-1H-pyrazolo(4,3-h)quinazoline-3-carboxylic acid

Product 1

HCID 135980700
8-anilino-N-hydroxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
Yield 66.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 260 mg (0.81 mmol) of 8-anilino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid in 50 mL of anhydrous dimethylformamide 111 mg of N-hydroxybenzotriazole (0.81 mmol), 0.16 mL of N-methylmorpholine, 205 mg (1.07 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 585 mg (2.13 mmol) of triphenylmethylhydroxylamine were added consecutively. After 48 hours at room temperature the solvent was removed under reduced pressure and the residue taken up with dichoromethane and washed with water. The organic layer was then dried over sodium sulfate and evaporated. The crude was treated with 10 mL of a mixture dichloromethanetrifluoroacetic acid and after 4 hours the volatiles were removed in vacuo. The residue was redissolved with dichoromethane and washed with aqueous NaHCO3 and the product purified by chromatography on a silica gel column, eluted with CH2Cl2-CH3COCH3 4/1, to give 180 mg (66% yield) of the title compound.

Workup

  1. customAfter 48 hours at room temperature the solvent was removed under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic layer was then dried over sodium sulfate
  4. customevaporated
  5. additionThe crude was treated with 10 mL of a mixture dichloromethanetrifluoroacetic acid and after 4 hours the volatiles
  6. customwere removed in vacuo
  7. dissolutionThe residue was redissolved with dichoromethane
  8. washwashed with aqueous NaHCO3
  9. customthe product purified by chromatography on a silica gel column
  10. washeluted with CH2Cl2-CH3COCH3 4/1

Sources & evidence

ORD record
ord-966dcc7a22fb4bdbbd2e4fd7ba7eb8a4
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08981089B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes