3-Fluorobenzylamine → HCID 178522847, compound

HRID 523377Notes

Reaction equation

HRID 523377 reaction equation
[OH:1][C@@H:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][NH:8][C:7](=[O:11])[C:6]=1[C:12]1[NH:13][C:14]2[C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH2:35].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>O.CN(C=O)C>[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34][NH:35][C:21]([C:20]1[C:14]2[NH:13][C:12]([C:6]3[C:7](=[O:11])[NH:8][CH:9]=[CH:10][C:5]=3[NH:4][CH2:3][C@@H:2]([OH:1])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:16][C:15]=2[CH:17]=[CH:18][CH:19]=1)=[O:22]

Participants

7

Reactant 4

HCID 668533-FluorobenzylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524247HCID 178524247, compound

Product 1

HCID 178522847HCID 178522847, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 100 mL round-bottomed flask, 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid (0.84 g, 2.15 mmol), 3-fluoro-benzylamine (296 mg, 270 μL, 2.37 mmol) and DIEA (612 mg, 827 μL, 4.73 mmol) were combined with DMF (10 mL) to give a black solution and to this was added HATU (982 mg, 2.58 mmol). The reaction was stirred at room temperature overnight. The next day, the reaction was dripped into water and the resulting precipitate was filtered and washed with water, ethyl ether, and hexanes. The purple solid was incompletely dissolved in minimal boiling ethanol and the resulting solid that formed upon cooling was filtered and washed with ethanol and hexanes yielding 2-[4-((S)-2-hydroxy-2-phenyl-ethylamino)-2-oxo-1,2-dihydro-pyridin-3-yl]-3H-benzoimidazole-4-carboxylic acid 3-fluoro-benzylamide as a light purple solid. LC/MS calcd for C28H24FN5O3 (m/e) 497.0, obsd 497.9 (M+H); 1H NMR (DMSO-d6-TFA) δ: 11.25 (br. s., 1H), 10.77 (br. s., 1H), 9.32 (t, J=5.8 Hz, 1H), 7.71-7.97 (m, 2H), 7.14-7.63 (m, 10H), 7.03-7.13 (m, 1H), 6.21 (d, J=7.5 Hz, 1H), 4.84 (br. s., 1H), 4.68 (br. s., 2H), 3.65 (d, J=12.5 Hz, 1H), 3.46 (d, J=7.0 Hz, 1H).

Workup

  1. customto give a black solution
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with water, ethyl ether, and hexanes
  4. dissolutionThe purple solid was incompletely dissolved
  5. customthe resulting solid that formed
  6. temperatureupon cooling
  7. filtrationwas filtered
  8. washwashed with ethanol and hexanes

Sources & evidence

ORD record
ord-98d2efffb5aa4f7e91f94e97755b0f56
Source dataset
uspto-grants-2016_05
Patent number
US09334480B2

Reaction notes

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