Phthalamide → HCID 22172592, compound

HRID 2055659Notes

Reaction equation

HRID 2055659 reaction equation
C(N)(=O)C1C(=CC=CC=1)C(N)=O.[CH2:13]([N:20]1[C:25](=[O:26])[C:24]2[CH:27]=[N:28][CH:29]=[CH:30][C:23]=2[N:22]=[C:21]1[CH:31]([N:35]([CH2:45][CH2:46][CH2:47][N:48]1C(=O)C2C(=CC=CC=2)C1=O)[C:36](=[O:44])[C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1)[CH:32]([CH3:34])[CH3:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.NN>CCO>[NH2:48][CH2:47][CH2:46][CH2:45][N:35]([C@@H:31]([C:21]1[N:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:25](=[O:26])[C:24]2[CH:27]=[N:28][CH:29]=[CH:30][C:23]=2[N:22]=1)[CH:32]([CH3:34])[CH3:33])[C:36](=[O:44])[C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1.[NH2:48][CH2:47][CH2:46][CH2:45][N:35]([CH:31]([C:21]1[N:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:25](=[O:26])[C:24]2[CH:27]=[N:28][CH:29]=[CH:30][C:23]=2[N:22]=1)[CH:32]([CH3:34])[CH3:33])[C:36](=[O:44])[C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 6956PhthalamideHCID 9321HydrazineHCID 22172645HCID 22172645, compound

Product 2

HCID 22172592HCID 22172592, compoundHCID 69316230HCID 69316230, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

Alternative Preparation of Formula I where R1, R3 and R4 are H; R5 is Benzyl; R6 is Isopropyl; R6′ is H; R7 is 3-Amino-propy; R8 is —C(O)—R9 where R9 is p-Methyl-phenyl-; W, Y and Z are —C═; and X is —N═: A phthalamide-protected precursor to Formula I, N-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[4,3-d]pyrimidin-2-yl)-2-methyl-propyl]-N-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]4-methyl-benzamide (300 mg, 0.488 mmol) and anhydrous hydrazine (98 mg, 3.06 mmol) in EtOH (12 mL) is refluxed for 3.0 h. The reaction is cooled to 5° C. and a precipitate is filtered off. The filtrate is concentrated in vacuo and purified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent) to provide the title compound, N-(3-amino-propyl)-N-[1-(3-benzyl-4-oxo-3,4-dihydro-pyrido[4,3-d]pyrimidin-2-yl)-2-methyl-propyl]4-methyl-benzamide.

Workup

  1. customAlternative Preparation of Formula I where R1, R3 and R4
  2. temperatureis refluxed for 3.0 h
  3. filtrationa precipitate is filtered off
  4. concentrationThe filtrate is concentrated in vacuo
  5. custompurified by flash chromatography (silica gel, 90:9:1 methylene chloride:methanol:ammonium hydroxide as eluent)

Sources & evidence

ORD record
ord-ded17e0e523e442da8da86c061ca4a03
Source dataset
uspto-grants-2008_02
Patent number
US07332498B2

Reaction notes

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