Triethylamine → HCID 178447228, compound

HRID 1591638Notes

Reaction equation

HRID 1591638 reaction equation
[CH3:1][CH:2]([CH2:6][CH3:7])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:28](=[O:29])[C:18]3=[CH:19][NH:20][C:21]4[C:22]([F:27])=[CH:23][CH:24]=[CH:25][C:26]=4[C:17]3=[N:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[F:27][C:22]1[C:21]2[NH:20][CH:19]=[C:18]3[C:28](=[O:29])[N:15]([C:12]4[CH:13]=[CH:14][C:9]([NH:8][C:3](=[O:4])[CH:2]([CH3:1])[CH2:6][CH3:7])=[CH:10][CH:11]=4)[N:16]=[C:17]3[C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 93697Butanoyl chloride, 2-methyl-HCID 178507702HCID 178507702, compound2×

Product 1

HCID 178447228HCID 178447228, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(±)-2-Methylbutyryl chloride (13.6 μl, 0.11 mmol) was added dropwise over 30 sec to a stirred solution of 2-(4-amino-phenyl)-6-fluoro-2,5-dihydro-pyrazolo[4,3-c]quinolin-3-one (Intermediate 2) (30 mg, 0.10 mmol), triethylamine (14 μl, 0.11 mmol) and 4-dimethylaminopyridine (2.4 mg, 0.02 mmol) in dichloromethane (1 ml) at room temperature. The mixture was stirred at room temperature for 16 h. The yellow solid was then filtered and purified by washing sequentially with a saturated solution of sodium bicarbonate (1 ml), ethyl acetate (1 ml) and ethyl alcohol (0.5 ml) and finally dried under suction to give the title compound (10 mg, 26%) as a bright yellow solid, LCMS m/z 379.36 [M+H]+ @ RT 1.18 min. δH(400 MHz, (CD3)2SO) 9.89 (1H, s), 8.52 (1H, s), 8.15 (2H, d J 9.0 Hz), 8.01 (1H, d J 7.0 Hz), 7.69 (2H, d J 9.0 Hz) 7.57-7.46 (2H, m), 2.46-2.39 (1H, m), 1.69-1.36 (2H, m), 1.11 (3H, d J 6.8 Hz), 0.91(3H, t J 7.3 Hz).

Workup

  1. filtrationThe yellow solid was then filtered
  2. custompurified
  3. washby washing sequentially with a saturated solution of sodium bicarbonate (1 ml), ethyl acetate (1 ml) and ethyl alcohol (0.5 ml)
  4. customfinally dried under suction

Sources & evidence

ORD record
ord-b97e0a4ceada4f8e929e98b089b27425
Source dataset
uspto-grants-2007_11
Patent number
US07291612B2

Reaction notes

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