Sodium Bicarbonate → HCID 66749516, compound

HRID 2401781Notes

Reaction equation

HRID 2401781 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[S:10][C:11]=2[C:12]2[N:16](S(N(C)C)(=O)=O)[CH:15]=[N:14][CH:13]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+]>Br.O.C(Cl)Cl>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[S:10][C:11]=2[C:12]2[NH:16][CH:15]=[N:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 66749081HCID 66749081, compound

Product 1

HCID 66749516HCID 66749516, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 260Hydrogen BromideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(4-(4-chlorobenzyl)-2-(pyridin-4-yl)thiazol-5-yl)-N,N-dimethyl-1H-imidazole-1-sulfonamide (50 mg, 0.109 mmol) in 48% HBr in water (3.0 mL) was heated to 90° C. for 2.5 hours. The cooled solution was taken up in DCM (20 mL) and saturated sodium bicarbonate (20 mL). The layers were separated and the aqueous extracted with DCM (20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. To this crude material was added the 19 mg of deprotected material obtained in the previous step. The combined material was purified by silica gel chromatography (methanol/DCM=0/100→315/85) to give 34 mg of the title compound as a white solid (27% yield). LC/MS (FA) ES+ 353. 1H NMR (300 MHz, d4-MeOH) δ: 8.63-8.61 (m, 2H), 7.93-7.91 (m, 2H), 7.80 (d, 1H, J=1.1 Hz), 7.30-7.19 (m, 5H), 4.35 (s, 2H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted with DCM (20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionTo this crude material was added the 19 mg of deprotected material
  7. customobtained in the previous step
  8. customThe combined material was purified by silica gel chromatography (methanol/DCM=0/100→315/85)

Sources & evidence

ORD record
ord-81ccef8a5f954bf69faddcfbdd57495c
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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