Phenylacetic Acid → HCID 58167999, compound

HRID 1029255Notes

Reaction equation

HRID 1029255 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:44]1[CH2:49][CH2:48][CH:47]([NH:50][C:51]2[CH:60]=[CH:59][N:58]=[C:57]3[C:52]=2[C:53]2[CH:65]=[CH:64][CH:63]=[CH:62][C:54]=2[C:55](=[O:61])[NH:56]3)[CH2:46][CH2:45]1>CN(C=O)C>[C:1]1([CH2:7][C:8]([N:44]2[CH2:45][CH2:46][CH:47]([NH:50][C:51]3[CH:60]=[CH:59][N:58]=[C:57]4[C:52]=3[C:53]3[CH:65]=[CH:64][CH:63]=[CH:62][C:54]=3[C:55](=[O:61])[NH:56]4)[CH2:48][CH2:49]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581681941-(4-Piperidinylamino)benzo[c][1,8]naphthyridin-6(5H)-one

Product 1

HCID 58167999HCID 58167999, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenylacetic acid (10 mg, 0.07 mmol), DIEA (28 mg, 0.22 mmol), and HATU (28 mg, 0.07 mmol) were dissolved in DMF (1 mL), and stirred for 30 min at room temperature. 358 (17 mg, 0.06 mmol) was added, and the reaction mixture was stirred for another 1 h at room temperature. The crude material was purified directly via HPLC to provide 360 (10 mg, 30% yield) as a solid. LC-MS (M+H=413, obsd.=413).

Workup

  1. stirringthe reaction mixture was stirred for another 1 h at room temperature
  2. customThe crude material was purified directly via HPLC

Sources & evidence

ORD record
ord-e8b94706ca18428b904db1b0df4e7c4f
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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