Sodium Iodide → HCID 56967031, compound

HRID 1468184Notes

Reaction equation

HRID 1468184 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]1[CH2:40][CH2:39][C:12]2[N:13]=[C:14]([NH:16][C:17](=[O:38])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][N:25]4[CH:29]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=5)[N:27]=[N:26]4)[CH:19]=3)[S:15][C:11]=2[CH2:10]1.[CH3:41][O:42][CH2:43][CH2:44]Br.C(N(CC)CC)C.[I-].[Na+]>CCO>[C:36]([C:33]1[CH:32]=[CH:31][C:30]([C:28]2[N:27]=[N:26][N:25]([CH2:24][C:20]3[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=3)[C:17]([NH:16][C:14]3[S:15][C:11]4[CH2:10][C@H:9]([NH:8][CH2:44][CH2:43][O:42][CH3:41])[CH2:40][CH2:39][C:12]=4[N:13]=3)=[O:38])[CH:29]=2)=[CH:35][CH:34]=1)#[N:37]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 809722-Bromoethyl methyl etherHCID 86672752HCID 86672752, compound

Product 1

HCID 56967031HCID 56967031, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

Add to a solution of N—((R)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-1,2,3-triazol-1-ylmethyl]-benzamide trifluoroacetate (0.92 g, 1.61 mmol), bromoethyl methyl ether (0.22 g, 1.61 mmol), triethylamine (0.33 g, 3.22 mmol) and sodium iodide (0.02 mg, 0.16 mmol) in 8 mL of EtOH. Heat the reaction mixture at 110° C. under microwave irradiation for 5 h. Filter the mixture, concentrate and purify via preparative HPLC to give 0.32 g, 39% yield of 3-[4-(4-cyano-phenyl)-[1,2,3]triazol-1-ylmethyl]-N—[(R)-6-(2-methoxy-ethylamino)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide as white foam. MS, ES+ 514.45 (M+H), rt 5.27 min

Workup

  1. customunder microwave irradiation for 5 h
  2. filtrationFilter the mixture
  3. concentrationconcentrate
  4. custompurify via preparative HPLC

Sources & evidence

ORD record
ord-7175b4055697432486d173dc5150bc4d
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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