Diisopropylethylamine → 5-Neopentyl-7-(2-oxo-2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)ethyl)-7,8-dihydro-1H-pyrazolo[3,4-g]quinolin-6(5H)-one

HRID 1985539Notes

Reaction equation

HRID 1985539 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)[C:12]2N=CC=CC=2N=[N:9]1.[CH2:25]([N:30]1[C:39]2[C:34](=[CH:35][CH:36]=[C:37]3NN=C[C:38]3=2)[CH2:33][CH:32]([CH2:43][C:44]([OH:46])=O)[C:31]1=[O:47])[C:26]([CH3:29])([CH3:28])[CH3:27].C(N(CC)C(C)C)(C)C.[O:57]=[C:58]1[N:67]([CH:68]2[CH2:73][CH2:72][NH:71][CH2:70][CH2:69]2)[CH2:66][C:65]2[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=2)[NH:59]1>ClCCl>[CH2:25]([N:30]1[C:39]2[CH:38]=[C:37]3[CH:12]=[N:8][NH:9][C:36]3=[CH:35][C:34]=2[CH2:33][CH:32]([CH2:43][C:44](=[O:46])[N:71]2[CH2:72][CH2:73][CH:68]([N:67]3[CH2:66][C:65]4[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=4)[NH:59][C:58]3=[O:57])[CH2:69][CH2:70]2)[C:31]1=[O:47])[C:26]([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110425973-(Piperidin-4-yl)-3,4-dihydroquinazolin-2(1H)-oneHCID 597319952-(1-neopentyl-2-oxo-2,3,4,7-tetrahydro-1H-pyrazolo[3,4-h]quinolin-3-yl)acetic acid

Product 1

HCID 119779715-Neopentyl-7-(2-oxo-2-(4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidin-1-yl)ethyl)-7,8-dihydro-1H-pyrazolo[3,4-g]quinolin-6(5H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (116 mg, 0.3 mmol) was added to a solution of 2-(1-neopentyl-2-oxo-2,3,4,7-tetrahydro-1H-pyrazolo[3,4-h]quinolin-3-yl)acetic acid (95 mg, 0.3 mmol) and N,N-diisopropylethylamine (158 μL, 0.9 mmol) in dichloromethane (5.0 mL). Mixture was stirred at room temperature for 45 minutes. 4-(2-Oxo-1,4-dihydro-2H-quinazolin-3-yl)piperidine (70 mg, 0.3 mmol) was then added to the mixture. After 3 h stirring at room temperature, the crude reaction mixture was purified by prep HPLC starting from 30% methanol in water to 90% methanol in water over a period of 8 min and at a flow rate of 40 ml/min. Removal of solvent furnished the desired. MS (ESI) 529 (M+H); Rf=1.57.

Workup

  1. stirringAfter 3 h stirring at room temperature
  2. customthe crude reaction mixture
  3. customwas purified by prep HPLC
  4. waitstarting from 30% methanol in water to 90% methanol in water over a period of 8 min and at a flow rate of 40 ml/min
  5. customRemoval of solvent
  6. customfurnished the

Sources & evidence

ORD record
ord-ce77bf29154d45f2b402b58b9a02403b
Source dataset
uspto-grants-2009_06
Patent number
US07544680B2

Reaction notes

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