Sodium Azide → HCID 86658255, compound

HRID 410658Notes

Reaction equation

HRID 410658 reaction equation
[OH:1][C@:2]1([C:14]2[S:15][C:16]([C:19]3[CH:24]=[C:23]([NH:25][C:26]4[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=4)[CH:22]=[C:21]([CH2:36]OS(C)(=O)=O)[CH:20]=3)=[CH:17][N:18]=2)[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[C:4]([CH3:13])([CH3:12])[CH2:3]1.[N-:42]=[N+:43]=[N-:44].[Na+]>CN1C(=O)CCC1>[N:42]([CH2:36][C:21]1[CH:20]=[C:19]([C:16]2[S:15][C:14]([C@@:2]3([OH:1])[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[C:4]([CH3:12])([CH3:13])[CH2:3]3)=[N:18][CH:17]=2)[CH:24]=[C:23]([NH:25][C:26]2[N:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][N:27]=2)[CH:22]=1)=[N+:43]=[N-:44]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86658254HCID 86658254, compound

Product 1

HCID 86658255HCID 86658255, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of the product of Step 1 (250 mg, 0.407 mmol) in anhydrous NMP (5 ml) was treated with sodium azide (132 mg, 2.034 mmol, 5.0 equiv) and stirred at 23° C. for 18 h. The reaction was partitioned between EtOAc (2×75 ml) and water (85 ml) and the combined organic layers were dried over Na2SO4, filtered and concentrated to afford methyl (1S,4R)-4-{5-[3-(azidomethyl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl]-1,3-thiazol-2-yl}-4-hydroxy-2,2-dimethylcyclohexanecarboxylate (220 mg, 96%), as an orange oil. MS ESI: [M+H]+ m/z 562.1

Workup

  1. customThe reaction was partitioned between EtOAc (2×75 ml) and water (85 ml)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d4486f40d6c4251ba1b8b9183eeda79
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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