HCID 67415937, compound → HCID 59743112, compound

HRID 1803598Notes

Reaction equation

HRID 1803598 reaction equation
C(O)=O.[CH2:4]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([NH:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:11]([CH3:29])=[C:12]([NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23](=[O:27])[NH:22][N:21]=[C:20]3Cl)=[O:16])[CH:13]=1)[CH3:5]>Cl.[Pd].CO>[CH2:4]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([NH:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:11]([CH3:29])=[C:12]([NH:14][C:15]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23](=[O:27])[NH:22][N:21]=[CH:20]3)=[O:16])[CH:13]=1)[CH3:5]

Participants

5

Reactant 1

HCID 67415937HCID 67415937, compound

Product 1

HCID 59743112HCID 59743112, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid [5-ethoxymethyl-2-methyl-3-(2-pyrrolidin-1-yl-ethylamino)-phenyl]-amide formic acid salt (55 mg, 0.104 mmol), 10% wet Pd/C (catalytic), 1 drop of conc. HCl and MeOH (4 mL) was evacuated and flushed (×3) with hydrogen. The reaction was stirred under a hydrogen balloon for 2.5 h. The reaction was filtered through celite, rinsed with MeOH and concentrated to yield 1-oxo-1,2-dihydro-phthalazine-6-carboxylic acid [5-ethoxymethyl-2-methyl-3-(2-pyrrolidin-1-yl-ethylamino)-phenyl]-amide (43 mg) as a tan solid. 1H NMR (400 MHz, d6-DMSO) δ: 1.16 (t, 3H), 1.93 (m, 4H), 2.00 (s, 3H), 2.53 (m, 4H), 3.47 (m, 6H), 4.39 (s, 2H), 5.23 (bs, 1H), 6.53 (s, 1H), 6.62 (s, 1H), 8.34 (s, 2H), 8.48 (s, 1H), 8.50 (s, 1H), 10.25 (s, 1H), 12.80 (s, 1H) ppm; m/z (M+1) 450.38.

Workup

  1. customwas evacuated
  2. customflushed (×3) with hydrogen
  3. filtrationThe reaction was filtered through celite
  4. washrinsed with MeOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-71b397c5528d40a58ede6910b9c7210b
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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