Hydrazine hydrate (1:1) → 8-(4-Fluorophenyl)-9-(1-methyl-1H-1,2,3-triazol-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

HRID 1968028Notes

Reaction equation

HRID 1968028 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:17]([C:18]3[N:19]=[N:20][N:21]([CH3:23])[CH:22]=3)[C:16](=O)[C:15]3[C:14]([C:25](OCC)=O)=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9]2)=[CH:4][CH:3]=1.[OH2:30].[NH2:31][NH2:32]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[NH:9][C:10]3[C:15]4[C:16](=[N:31][NH:32][C:25](=[O:30])[C:14]=4[CH:13]=[CH:12][CH:11]=3)[CH:17]2[C:18]2[N:19]=[N:20][N:21]([CH3:23])[CH:22]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67261815Ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-1,2,3-triazol-4-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1359984208-(4-Fluorophenyl)-9-(1-methyl-1H-1,2,3-triazol-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-oneYield 39%

Procedure

A mixture of ethyl 2-(4-fluorophenyl)-3-(1-methyl-1H-1,2,3-triazol-4-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (113 mg, 0.28 mmol) in 85% hydrazine monohydrate (4 mL) stirred for 3 hr at room temperature. The mixture was filtered and washed with water, petroleum ether and ethyl acetate to give the crude product, which was purified by prep-HPLC to give the title compound (41 mg, yield 39%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.93 (s, 3H), 4.50-4.52 (d, J=7.6 Hz, 1H), 4.96-4.98 (d, J=7.6 Hz, 1H), 7.09-7.15 (m, 3H), 7.35-7.42 (m, 4H), 7.55-7.57 (t, J=7.6 Hz, 1H), 7.72 (s, 1H); LC-MS (ESI) m/z: 363 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with water, petroleum ether and ethyl acetate
  3. customto give the crude product, which
  4. customwas purified by prep-HPLC

Sources & evidence

ORD record
ord-73fad23c7e0145b396fe9b75e45dd3f1
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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