Methyl 2-isocyanato-2-methylpropanoate → methyl 2-methyl-2-[[3-[(4-oxo-5,6,7,8-tetrahydro-3H-phthalazin-1-yl)methyl]phenyl]carbamoylamino]propanoate

HRID 1012958Notes

Reaction equation

HRID 1012958 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][N:7]=1.[CH3:20][O:21][C:22](=[O:29])[C:23]([N:26]=[C:27]=[O:28])([CH3:25])[CH3:24]>C(Cl)Cl>[CH3:24][C:23]([NH:26][C:27](=[O:28])[NH:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:4]([CH2:5][C:6]2[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[NH:8][N:7]=2)[CH:3]=1)([CH3:25])[C:22]([O:21][CH3:20])=[O:29]

Participants

4

Reactant 2

HCID 2769374Methyl 2-isocyanato-2-methylpropanoateHCID 59755755HCID 59755755, compound

Product 1

HCID 57786643methyl 2-methyl-2-[[3-[(4-oxo-5,6,7,8-tetrahydro-3H-phthalazin-1-yl)methyl]phenyl]carbamoylamino]propanoateYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-amino-benzyl)-5,6,7,8-tetrahydro-2H-phthalazin-1-one (4) (50 mg, 0.195 mmol) in dry DCM (10 ml) was added 2-isocyanato-2-methyl-propionic acid methyl ester (60 mg, 0.428 mmol). The resulting solution was stirred for 2 days, washed with water (3×10 ml), dried over sodium sulphate and concentrated in vacuo to yield a semi-crystalline solid (44 mg).

Workup

  1. washwashed with water (3×10 ml)
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fb0b81580c6406faaf3f76dd36e771f
Source dataset
uspto-grants-2011_07
Patent number
US07981890B2

Reaction notes

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