Hydrochloric Acid → HCID 86639693, compound

HRID 1426154Notes

Reaction equation

HRID 1426154 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:22]CCC(OC)=O)[CH:12]=[N:13][C:14]=1[NH:15][C:16]1[S:17][CH:18]=[C:19]([CH3:21])[N:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[Cl:35][C:36]1[CH:41]=[C:40]([N+]([O-])=O)[CH:39]=[CH:38][N:37]=1.[NH4+].[Cl-:46].Cl>CS(C)=O>[ClH:35].[ClH:46].[CH2:1]([O:8][C:9]1[C:14]([NH:15][C:16]2[S:17][CH:18]=[C:19]([CH3:21])[N:20]=2)=[N:13][CH:12]=[C:11]([S:22][C:40]2[CH:39]=[CH:38][N:37]=[C:36]([Cl:35])[CH:41]=2)[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 7351522-Chloro-4-nitropyridineHCID 16660505Methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86639693HCID 86639693, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 1 dram vial was charged with methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)propanoate (70 mg, 0.168 mmol) and DMSO (2 mL). Potassium 2-methylpropan-2-olate (56.7 mg, 0.505 mmol) was added and the reaction was stirred for 5 minutes. 2-Chloro-4-nitropyridine (53.4 mg, 0.337 mmol) was added and the reaction was stirred for 10 minutes. The reaction was poured into saturated aqueous NH4Cl and extracted with EtOAc. The organic phase was washed with water. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified on a silica gel column (20% EtOAc/hexanes) to afford the title compound (45.7 mg, 52.8% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 10.92, (bs, 1H), 8.15 (m, 2H), 7.69 (d, 1H), 7.56 (m, 2H), 7.43-7.32 (m, 3H), 7.10 (d, 1H), 6.97 (dd, 1H), 6.80 (s, 1H), 5.34 (s, 2H), 2.30 (s, 3H). Mass spectrum (apci) m/z=441.0 (M+H-2HCl).

Workup

  1. stirringthe reaction was stirred for 10 minutes
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on a silica gel column (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c99a5b07c6fa41cfbfd5b4e8df12102a
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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