Ammonium Chloride → HCID 44553786, compound

HRID 714398Notes

Reaction equation

HRID 714398 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][N:20]=3)[C:15](O)=[O:16])[C:8]2=[O:21])=[CH:4][CH:3]=1.C([N:27](C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][N:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][N:20]=3)[C:15]([NH2:27])=[O:16])[C:8]2=[O:21])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27960291-Hydroxybenzotriazole hydrateHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44553786HCID 44553786, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid (0.35 g, 1.11 mmol), diisopropylethylamine (0.58 g, 4.44 mmol), 1-hydroxybenzotriazole monohydrate (0.30 g, 2.22 mmol) and O-(1H-benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.71 g, 2.22 mmol) and ammonium chloride (0.36 g, 6.66 mmol) in tetrahydrofuran (10 mL) was stirred at ambient temperature for 23 hours and concentrated in vacuo. The residue was dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate solution (15 mL) and water (30 mL). The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide as a colorless solid (0.14 g, 40%): mp 206-208° C.; 1H NMR (300 MHz, CDCl3) δ 8.68 (s, 1H), 8.34 (d, 4.8 Hz, 1H), 8.13 (s, 1H), 7.62 (s, 1H), 7.33-7.13 (m, 5H), 4.38 (s, 2H), 3.92 (t, J=7.8 Hz, 2H), 3.34 (t, J=8.1 Hz, 2H); MS (ES+) m/z 314.9 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium bicarbonate solution (15 mL) and water (30 mL)
  4. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f87717f55914148a4e3d39a2c6d089a
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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