Ammonium Chloride → HCID 178478061, compound

HRID 2401891Notes

Reaction equation

HRID 2401891 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][C:6]1[N:7]=[C:8]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[S:9][C:10]=1[CH2:11][C:12]#[N:13].[N-:24]=[N+:25]=[N-:26].[Na+].[NH4+].[Cl-]>CN(C=O)C.C(OCC)(=O)C.O>[NH:24]1[C:12]([CH2:11][C:10]2[S:9][C:8]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)=[N:7][C:6]=2[CH2:5][C:4]2[CH:20]=[CH:21][C:22]([Cl:23])=[C:2]([Cl:1])[CH:3]=2)=[N:13][N:26]=[N:25]1

Participants

7

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 66747563HCID 66747563, compound

Product 1

HCID 178478061HCID 178478061, compoundYield 5.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-(3,4-dichlorobenzyl)-2-morpholinothiazol-5-yl)acetonitrile (87.0 mg, 0.236 mmol) in DMF (0.74 mL) was added sodium azide (21.6 mg, 0.332 mmol) and NH4Cl (17.8 mg, 9.53 mmol) and the resulting mixture was heated to 140 degrees overnight. More sodium azide (43 mg, 0.66 mmol) and NH4Cl (36 mg, 19 mmol) were added and the reaction was heated to 120 degrees overnight. The reaction was cooled and taken up in ethyl acetate (25 mL) and water (5 ml). The layers were separated and the organic layer was washed with water (3×5 mL).). The organic layer was dried and concentrated in vacuo. The residue was purified by preparative reverse phase chromatography to give 5 mg (5% yield) of the title compound as a white solid LC/MS (FA) ES+ 411. 413. 1H NMR (400 MHz, DMSO-d6) δ: 7.50 (d, 1H, J=8.0 Hz), 7.46 (d, 1H, J=2.0 Hz), 7.20 (dd, 1H, J=8.0, 2.0 Hz), 4.41 (s, 2H), 3.88 (s, 2H), 3.65-3.62 (m, 4H), 3.32 (bs, 1H), 3.26-3.24 (m, 4H).

Workup

  1. temperaturethe resulting mixture was heated to 140 degrees overnight
  2. temperaturethe reaction was heated to 120 degrees overnight
  3. temperatureThe reaction was cooled
  4. customThe layers were separated
  5. washthe organic layer was washed with water (3×5 mL)
  6. customThe organic layer was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative reverse phase chromatography

Sources & evidence

ORD record
ord-371ac9c714584e9f8de98dba0dd658b3
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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