Ammonium Chloride → HCID 121447882, compound

HRID 1048890Notes

Reaction equation

HRID 1048890 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:19]([O:21]CC)=O)=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N:25]([CH3:33])[CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1.[Cl-].[NH4+].F[P-](F)(F)(F)(F)F.C[N:44](C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:19]([NH2:44])=[O:21])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][C:3]=1[N:25]([CH3:33])[CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 121447978HCID 121447978, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 121447882HCID 121447882, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound U (26 mg, 0.062 mmol, 1.0 eq), ammonium chloride (6.6 mg, 0.12 mmol, 2.0 eq), (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (28 mg, 0.074 mmol, 1.2 eq) and N,N-diisopropylethylamine (43 μL, 0.25 mmol, 4.0 eq) were dissolved in DMF (0.5 mL) and stirred overnight. The reaction was diluted with ethyl acetate and washed with water (2×). The aqueous phase was back extracted with ethyl acetate and the combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by reverse phase chromatography afforded 7.0 mg (27%) of the title compound as white solid. 1H NMR (400 MHz, DMSO-d6) δ 9.21 (d, J=4.4 Hz, 1H), 8.48-8.45 (m, 3H), 7.76-7.72 (m, 3H), 7.67 (dt, J=7.8, 1.7 Hz, 1H), 7.58 (d, J=4.4 Hz, 1H), 7.51 (t, J=8.7 Hz, 2H), 7.35 (dd, J=7.7, 4.9 Hz, 1H), 6.81 (d, J=14.0 Hz, 1H), 4.41 (s, 2H), 2.83 (s, 3H); ES-MS [M+1]+: 421.2.

Workup

  1. washwashed with water (2×)
  2. extractionThe aqueous phase was back extracted with ethyl acetate
  3. dry with materialthe combined organics were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-70f4a9f5150a40feb295a781fdc62547
Source dataset
uspto-grants-2016_07
Patent number
US09382208B1

Reaction notes

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