HCID 16637187, compound → HCID 22993961, compound

HRID 1167828Notes

Reaction equation

HRID 1167828 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH:10]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:5][C:6]=1[C:7](=[S:9])[NH2:8].Br[CH2:31][C:32]([C:34]1[CH:35]=[C:36]([NH:40][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:37]=[CH:38][CH:39]=1)=O>CO>[NH2:10][C:4]1[S:5][C:6]([C:7]2[S:9][CH:31]=[C:32]([C:34]3[CH:35]=[C:36]([NH:40][C:41](=[O:48])[C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:37]=[CH:38][CH:39]=3)[N:8]=2)=[C:2]([NH2:1])[N:3]=1

Participants

4

Reactant 2

HCID 16637187HCID 16637187, compoundHCID 54012078HCID 54012078, compound

Product 1

HCID 22993961HCID 22993961, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-amino-2-(trityl-amino)-thiazole-5-carbothioic acid amide (304 mg, 0.73 mmol) and N-(3-Bromoacetyl-phenyl)-benzamide (300 mg, 0.94 mmol) in MeOH (30 ml) was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was dissolved in EtOAc (100 ml). The EtOAc solution was washed with a saturated aqueous solution of NaHCO3 (3×25 ml). The organic layer was separated, dried over MgSO4, and concentrated. Purification of the residue was achieved by silica gel chromatography (75% EtOAc/DCM) providing N-[3-(2′,4′-diamino-[2,5′]bithiazolyl-4-yl)-phenyl]-benzamide (110 mg, 39% yield). mp 159-163° C. (decomp). 1H NMR (CD3OD): δ 8.33 (s, 1H), 8.00-7.97 (m, 2H), 7.75-7.71 (m, 2H), 7.64-7.52 (m, 3H), 7.43 (t, J=7.74 Hz, 1H), 7.33 (s, 1H). FABMS Calcd for C19H15N5OS2: 394.0796. Found: 394.0802.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (100 ml)
  3. washThe EtOAc solution was washed with a saturated aqueous solution of NaHCO3 (3×25 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification of the residue

Sources & evidence

ORD record
ord-9a0b8e7357c8499b8075ba8c460503a5
Source dataset
uspto-grants-2003_09
Patent number
US06620828B2

Reaction notes

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