Benzylamine → HCID 66927211, compound

HRID 1404130Notes

Reaction equation

HRID 1404130 reaction equation
[CH2:1]([O:3][C:4]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6]([CH2:15][C:16]([OH:18])=O)=[CH:7][N:8]2[CH3:14])[CH3:2].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.[C:52]1([CH2:58][NH2:59])[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>C1COCC1.C(OCC)(=O)C.O>[CH2:58]([NH:59][C:16](=[O:18])[CH2:15][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:12]([F:13])[C:4]=2[O:3][CH2:1][CH3:2])[N:8]([CH3:14])[CH:7]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58303999HCID 58303999, compound

Product 1

HCID 66927211HCID 66927211, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 30-13 (30 mg, 0.12 mmol), HATU (76 mg, 0.2 mmol), DIPEA (39 mg, 0.3 mmol) and phenylmethanamine (17 mg, 0.16 mmol) in THF (5 mL) was stirred at room temperature overnight. Water (5 mL) and ethyl acetate (10 mL) were added to the mixture. The organic layer was separated, washed with brine (3×20 mL), dried over MgSO4, filtered and evaporated to give a crude product, which was purified by preparative TLC (petroleum ether/ethyl acetate=1:1) to afford 30-14 (28 mg, 69%) as a light yellow solid. LRMS: calc 340.2 and found: 341.1 [M+1].

Workup

  1. customThe organic layer was separated
  2. washwashed with brine (3×20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a crude product, which
  7. customwas purified by preparative TLC (petroleum ether/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-33ec4d493f244186b824691ac07963f2
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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