Dimethylbarbituric acid → HCID 25234731, compound

HRID 1670588Notes

Reaction equation

HRID 1670588 reaction equation
C([N:4]([C:31]1[S:32][CH:33]=[CH:34][N:35]=1)[S:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:18][CH2:17][C@H:16]([N:19]3[C:28]4[C:23](=[CH:24][C:25]([Cl:29])=[CH:26][CH:27]=4)[CH2:22][CH2:21][CH2:20]3)[C:15]2=[O:30])=[CH:12][CH:13]=1)(=[O:7])=[O:6])C=C.CN1C(=O)CC(=O)N(C)C1=O>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].C(#N)C>[Cl:29][C:25]1[CH:24]=[C:23]2[C:28](=[CH:27][CH:26]=1)[N:19]([C@H:16]1[CH2:17][CH2:18][N:14]([C:11]3[N:10]=[CH:9][C:8]([S:5]([NH:4][C:31]4[S:32][CH:33]=[CH:34][N:35]=4)(=[O:6])=[O:7])=[CH:13][CH:12]=3)[C:15]1=[O:30])[CH2:20][CH2:21][CH2:22]2

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 25234774HCID 25234774, compound

Product 1

HCID 25234731HCID 25234731, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Prepared using General Procedure 5. The (S)-N-allyl-6-(3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide (94 mg, 0.18 mmol), 1,3-dimethylbarbituric acid (166 mg, 1.06 mmol), and palladium-tetrakis(triphenylphosphine) (42 mg, 0.036 mmol) were combined in a flask and the flask placed under N2. Acetonitrile (1.2 mL) was then added and the suspension was heated to 60° C. After 1.5 hours the suspension was filtered and concentrated. The residue was purified by mass-trigger LC/MS (10%-99% CH3CN/H2O (0.05% TFA)) over 15 minutes to yield (S)-6-(3-(6-chloro-3,4-dihydroquinolin-1(2H)-yl)-2-oxopyrrolidin-1-yl)-N-(thiazol-2-yl)pyridine-3-sulfonamide. LC/MS (10%-99% CH3CN/H2O (0.05% TFA)), m/z: M+1 obs=490.3, tR=1.81 min.

Workup

  1. customPrepared
  2. filtrationAfter 1.5 hours the suspension was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by mass-trigger LC/MS (10%-99% CH3CN/H2O (0.05% TFA)) over 15 minutes

Sources & evidence

ORD record
ord-c022f37923574748aa75c231eeb2d864
Source dataset
uspto-grants-2011_08
Patent number
US07994174B2

Reaction notes

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