Water → HCID 66819583, compound

HRID 2092353Notes

Reaction equation

HRID 2092353 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:12](=[CH:13][C:14]4[CH2:20][CH2:19][CH2:18][C:15]=4[CH:16]=3)[NH:11][C:10](=[O:21])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.O.[CH3:23][N:24]1C(=O)N(C)CCC1>>[O:21]=[C:10]1[CH2:9][CH:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[C:23]#[N:24])[C:17]2[C:12](=[CH:13][C:14]3[CH2:20][CH2:19][CH2:18][C:15]=3[CH:16]=2)[NH:11]1

Participants

4

Reactant 3

HCID 962WaterHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 2942381HCID 2942381, compound

Product 1

HCID 66819583HCID 66819583, compound

Conditions

Temperature
195 °C

Procedure

A mixture of 4-(3-Bromo-phenyl)-1,3,4,6,7,8-hexahydro-cyclopenta[g]quinolin-2-one (160 mg, 0.47 mmol) and cuprous cyanide (50.3 mg, 0.56 mmol) in N,N′-dimethylpropyleneurea was heated at 195° C. for 14 hr under an atmosphere of argon. Water was added and the product extracted with ethyl acetate. The product (12 mg) was purified by flash chromatography on silica gel (eluent, hexane:ethyl acetate, 8:2, 7:3, 6:4) followed by reverse phase HPLC (water-acetonitrile gradient, 0.05% trifluoroacetic acid, 70:30 to 10:90, 20 min, linear gradient; flow, 15 ml/min; column, Phenomenex Luna 5μ C18, 100×21.2 mm; UV 254 and 218 nm).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. customThe product (12 mg) was purified by flash chromatography on silica gel (eluent, hexane:ethyl acetate, 8:2, 7:3, 6:4)
  3. customfollowed by reverse phase HPLC (water-acetonitrile gradient, 0.05% trifluoroacetic acid, 70:30 to 10:90, 20 min, linear gradient; flow, 15 ml/min; column, Phenomenex Luna 5μ C18, 100×21.2 mm; UV 254 and 218 nm)

Sources & evidence

ORD record
ord-8d24ebf7ed7b41c397aa9e690442048f
Source dataset
uspto-grants-2013_05
Patent number
US08440705B2

Reaction notes

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