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Triethylamine → 2-{3-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic Acid Methyl Ester

HRID 1012956
Notes
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Reaction equation

HRID 1012956 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15](=[O:22])[NH:14][N:13]=2)=[CH:7][C:3]=1C(O)=O.C([N:25]([CH2:28]C)CC)C.Cl.[CH3:31][O:32][C:33](=[O:37])[C@H:34]([CH3:36])[NH2:35].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:45])C=CC=CC=1>C(#N)C.CN1CCCC1=O>[CH3:31][O:32][C:33](=[O:37])[CH:34]([NH:35][C:28]([NH:25][C:3]1[CH:7]=[C:8]([CH2:11][C:12]2[C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[C:15](=[O:22])[NH:14][N:13]=2)[CH:9]=[CH:10][C:2]=1[F:1])=[O:45])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2733257Alanine methyl ester hydrochlorideHCID 250050192-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-benzoic acid

Product 1

HCID 577866402-{3-[2-Fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)-phenyl]-ureido}-propionic Acid Methyl Ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 2-fluoro-5-(4-oxo-3,4,5,6,7,8-hexahydro-phthalazin-1-ylmethyl)benzoic acid (11) (0.50 g, 1.650 mmol), in acetonitrile (2.5 ml) was added triethylamine (0.46 ml, 3.31 mmol) the suspension dissolved to afford a brown solution which was subsequently heated to 85° C. D/L alanine methyl ester hydrochloride (2.30 g, 1.650 mmol) dissolved in acetonitrile (5 ml) and N-methylpyrrolidinone (0.5 ml) was added simultaneously to the reaction mixture with diphenylphosphinic azide (0.357 ml, 1.650 mmol). After 40 minutes of heating the reaction mixture was cooled to ambient temperature and concentrated to vacuo. The crude oil was then subjected to flash chromatography, eluent hexane/ethyl acetate, 7:13 (Rf=0.14). Single peak in LC-MS, (0.67 g, 98% purity); m/z (LC-MS, ESP), RT=3.37 mins (M+H 403.2).

Workup

  1. dissolutiondissolved
  2. customto afford a brown solution which
  3. temperatureAfter 40 minutes of heating the reaction mixture
  4. temperaturewas cooled to ambient temperature
  5. concentrationconcentrated to vacuo

Sources & evidence

ORD record
ord-f745de5a42854b289975365c67a7309a
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07981890B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes