Benzoic Acid → HCID 58504550, compound

HRID 2367618Notes

Reaction equation

HRID 2367618 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:43][C@@H:44]1[CH2:49][CH2:48][CH2:47][N:46]([C:50]2[N:55]=[C:54]([NH:56][CH3:57])[N:53]=[C:52]([C:58]3[CH:65]=[CH:64][C:61]([C:62]#[N:63])=[C:60]([F:66])[CH:59]=3)[CH:51]=2)[CH2:45]1>CN(C=O)C.O>[C:62]([C:61]1[CH:64]=[CH:65][C:58]([C:52]2[N:53]=[C:54]([NH:56][CH3:57])[N:55]=[C:50]([N:46]3[CH2:47][CH2:48][CH2:49][C@@H:44]([NH:43][C:1](=[O:9])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH2:45]3)[CH:51]=2)=[CH:59][C:60]=1[F:66])#[N:63]

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58504604HCID 58504604, compound

Product 1

HCID 58504550HCID 58504550, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To benzoic acid (30.6 mg, 0.250 mmol) in DMF (2 mL) was added HATU (105 mg, 0.275 mmol) followed by Hunig's base (0.18 mL, 1.00 mmol). After 15 minutes, 4-[6-[(3R)-3-amino-1-piperidinyl]-2-(methylamino)-4-pyrimidinyl]-2-fluorobenzonitrile (100 mg, 0.250 mmol) was added, and the reaction mixture was stirred at room temperature for 30 minutes. Water was added (˜10 mL), and a solid precipitated. The mixture was filtered, and the solid was washed with water and air dried to afford the crude title compound (83 mg) as a yellow solid. LC-MS (ES) m/z=431 [M+H]+.

Workup

  1. customa solid precipitated
  2. filtrationThe mixture was filtered
  3. washthe solid was washed with water and air
  4. customdried

Sources & evidence

ORD record
ord-fa45968a8b374735ae0133a43f545fb8
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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