Hydrazine hydrate (1:1) → 8-(4-(4-(cyclopropanecarbonyl) piperazine-1-carbonyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

HRID 907874Notes

Reaction equation

HRID 907874 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[CH:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:28](=O)[C:27]5[C:26]([C:37]([O:39]C)=O)=[CH:25][CH:24]=[CH:23][C:22]=5[NH:21]4)=[CH:16][CH:15]=3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1.O.[NH2:42][NH2:43]>>[CH:1]1([C:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]4[NH:21][C:22]5[C:27]6[C:28](=[N:42][NH:43][C:37](=[O:39])[C:26]=6[CH:25]=[CH:24][CH:23]=5)[CH:29]4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:16][CH:15]=3)=[O:13])[CH2:8][CH2:7]2)=[O:5])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260447Methyl 2-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1363851878-(4-(4-(cyclopropanecarbonyl) piperazine-1-carbonyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-oneYield 19%

Procedure

A mixture of methyl 2-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (300 mg, 0.55 mmol) and hydrazine monohydrate (3 mL) was stirred room temperature for 3 h. The resulting mixture was evaporated under reduced pressure to 10 mL and then filtered; the filtrate was concentrated to give the crude product. The crude product was purified by pre-HPLC to give 8-(4-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one as a white solid (4 mg, yield 19%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.71-0.74 (m, 4H), 1.97 (t, 1H), 3.46-3.76 (m, 8H), 4.36 (dd, 1H), 4.83 (dd, 1H), 7.13-7.23 (m, 6H), 7.30 (d, 2H), 7.38 (t, 3H), 7.47 (s, 1H), 7.59 (t, 1H), 12.17 (s, 1H); LC-MS (ESI) m/z: 520(M+1)+.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure to 10 mL
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. customto give the crude product
  5. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-dea49d764d8a420687689d8ac2f68659
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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