Potassium Hydroxide → HCID 136027629, compound

HRID 1428864Notes

Reaction equation

HRID 1428864 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:13]2[NH:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][C:17]([N:24]([CH3:26])[CH3:25])=[CH:18][CH:19]=3)[N:14]=2)[CH:12]=1)=[O:7])C.C(OC(C1C=NN(C2NC(=O)C3C(=CC=CC=3N(C)C)N=2)C=1)=O)C.CN(C)C1C=C2C(C(=O)NC(N3C=C(C(O)=O)C=N3)=N2)=CC=1>C1COCC1>[CH3:25][N:24]([CH3:26])[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]2[C:16]=1[C:21](=[O:23])[NH:22][C:13]([N:11]1[CH:12]=[C:8]([C:6]([OH:5])=[O:7])[CH:9]=[N:10]1)=[N:14]2

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 136027596HCID 136027596, compoundHCID 136337183HCID 136337183, compoundHCID 136337184HCID 136337184, compound

Product 1

HCID 136027629HCID 136027629, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1M KOH (3.8 mL, 3.8 mmol) was added to a 3:2 mixture of 1-(7-dimethylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester and 1-(5-dimethylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (0.415 g, 1.27 mmol) in THF (3.8 mL). The reaction mixture was allowed to stir at room temperature for 18 h and was then concentrated. The residue was re-dissolved in water (10 mL) and acidified with aqueous HCl (1 M, 3 mL). The resulting precipitate was collected by filtration to yield a mixture of the titled compound and 1-(7-dimethylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid. The collected precipitate was triturated from DMSO and rinsed with ethanol to yield pure 1-(7-dimethylamino-4-oxo-3,4-dihydro-quinazolin-2-yl)-1H-pyrazole-4-carboxylic acid. The filtrate from the trituration was purified by reverse-phase HPLC to yield the titled compound (49.7 mg, 13% yield). MS (ESI/Cl): mass calcd. for C14H13N5O3, 299.1; m/z found, 300.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 12.99 (s, 2H), 8.96 (d, J=0.6 Hz, 1H), 8.25 (s, 1H), 7.84 (t, J=8.1 Hz, 1H), 7.67-7.48 (m, 2H), 3.12 (s, 6H).

Workup

  1. concentrationwas then concentrated
  2. dissolutionThe residue was re-dissolved in water (10 mL)
  3. filtrationThe resulting precipitate was collected by filtration
  4. customto yield

Sources & evidence

ORD record
ord-b262f43ed0524437a5995ac0fd8e0def
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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