Triethylamine → HCID 16066668, compound

HRID 1455611Notes

Reaction equation

HRID 1455611 reaction equation
[N:1]1([CH2:10][C:11]([OH:13])=O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:38][C:39]1[CH:40]=[C:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:42]=[CH:43][CH:44]=1.C(N(CC)CC)C>C(#N)C.CO>[N:1]1([CH2:10][C:11]([NH:38][C:39]2[CH:40]=[C:41]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:42]=[CH:43][CH:44]=2)=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 167173-AminobiphenylHCID 805645Benzoimidazol-1-yl-acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 16066668HCID 16066668, compoundYield 19.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

(1H-Benzimidazol-1-yl)acetic acid (triethylamine salt) (315 mg, 1.1 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexaflurophosphate (520 mg, 1.4 mmol), 3-amino biphenyl (290 mg, 1.6 mmol) and triethylamine (0.6 mL, 4.4 mmol) in acetonitrile (10 mL) was stirred at room temperature for 24 h. Methanol (10 mL) was then added and evaporated to dryness in vacuo. The crude mixture was then passed through a silica gel column eluting with ethyl acetate:methanol (1% up to 3% methanol). The product was collected and dried, dissolved in methanol and 1 M hydrogen chloride in diethyl ether (0.5 mL) added and product crystallised, filtered and dried to give the title compound as a white solid (70 mg, 17%). 1H NMR (400 MHz, CD3OD+1 drop of DMSO-d6) δ ppm 5.55 (2H, s), 7.32-7.35 (1H, m), 7.40-7.44 (4H, m), 7.56-7.59 (3H, m), 7.67-7.72 (2H, m), 7.89-7.96 (3H, m), 9.54 (1H, s). MS (ES) m/z 327.9 [M+H]+.

Workup

  1. customevaporated to dryness in vacuo
  2. washeluting with ethyl acetate
  3. customThe product was collected
  4. customdried
  5. dissolutiondissolved in methanol
  6. addition1 M hydrogen chloride in diethyl ether (0.5 mL) added
  7. customproduct crystallised
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-f4db038a0b5a4b5aa66fda49c1ce647b
Source dataset
uspto-grants-2009_01
Patent number
US07482469B2

Reaction notes

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