Ammonium Chloride → HCID 59853002, compound

HRID 1670283Notes

Reaction equation

HRID 1670283 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[C:6]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=2[F:28])[CH:5]=[CH:4][N:3]=1.C1C[N:32]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH4+].[Cl-]>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([NH2:32])=[O:17])=[CH:12][CH:13]=2)=[C:6]([O:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=2[F:28])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 59852905HCID 59852905, compound

Product 1

HCID 59853002HCID 59853002, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-(2-amino-4-(2-fluoro-4-nitrophenoxy)pyridin-3-yl)phenyl)acetic acid (65 mg, 0.17 mmol) in anhydrous DMF (1.2 mL) was treated with PyBOP (125 mg, 0.24 mmol) and HOBt (32 mg, 0.24 mmol) followed by DIPEA (60 μL, 0.35 mmol) and NH4Cl (19 mg, 0.35 mmol). After stirring at room temperature for 20 min, the mixture was concentrated under vacuum and the residue partitioned between EtOAc and saturated aq. NaHCO3 solution. The EtOAc phase was washed with brine, dried (MgSO4) and concentrated in vacuo. The product was purified by flash column chromatography on SiO2 eluting with 0-8% MeOH/CH2Cl2 to give the title compound (40 mg, 62%) as an amber colored oil. 1H NMR (DMSO-d6) δ 8.23 (dd, 1H, J=10.7, 2.5 Hz), 8.05 (d, 1H, J=9.2 Hz), 7.93 (d, 1H, J=6.1 Hz), 7.42-7.32 (m, 2H), 7.33-7.25 (m, 4H), 6.92 (s, 1H), 6.25 (d, 1H, J=5.6 Hz), 5.64 (s, 2H), 3.36 (s, 2H); MS (ESI+): m/z 383.17 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. customthe residue partitioned between EtOAc and saturated aq. NaHCO3 solution
  3. washThe EtOAc phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by flash column chromatography on SiO2 eluting with 0-8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1e398c13174742f9ad757aafb964a793
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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