Triethylamine → HCID 67161288, compound

HRID 469527Notes

Reaction equation

HRID 469527 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][S:11][C:5]=2[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3]1.C(N(CC)CC)C.[F:25][C:26]1[CH:27]=[C:28]([CH2:33][C:34](O)=[O:35])[CH:29]=[C:30]([F:32])[CH:31]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[F:25][C:26]1[CH:27]=[C:28]([CH2:33][C:34]([NH:1][N:2]2[C:7](=[O:8])[C:6]3[CH:9]=[CH:10][S:11][C:5]=3[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:3]2)=[O:35])[CH:29]=[C:30]([F:32])[CH:31]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1454243,5-Difluorophenylacetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67161596HCID 67161596, compound

Product 1

HCID 67161288HCID 67161288, compoundYield 12.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Example 9B (31.6 mg, 0.13 mmol), triethylamine (0.028 mL, 0.20 mmol), 2-(3,5-difluorophenyl)acetic acid (25.4 mg, 0.15 mmol), and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (49.8 mg, 0.16 mmol) in DMF (0.4 mL) was stirred overnight, diluted with EtOAc, washed with 1 N NaOH and brine, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (12% EtOAc/CH2Cl2) to give the title compound as a white solid (6.2 mg, 0.016 mmol). 1H NMR (300 MHz, DMSO-d6) δ 11.80 (s, 1H), 8.24 (d, J=5.2 Hz, 1H), 7.87-7.77 (m, 3H), 7.64-7.55 (m, 3H), 7.22-7.08 (m, 3H), 3.78 (s, 2H); MS (ESI−) M/Z 396.1 (M−H)−.

Workup

  1. washwashed with 1 N NaOH and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe residue was chromatographed on SiO2 (12% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-6bc652bb11654d36a02329d0c4f517e3
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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