1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86643340, compound

HRID 1948327Notes

Reaction equation

HRID 1948327 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH2:23]O)[N:22]=2)[CH2:14][C@@H:13]1[O:30][CH3:31])=[O:10].C1(P([N:46]=[N+:47]=[N-:48])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:46]([CH2:23][C:21]1[N:22]=[C:18]([N:15]2[CH2:16][CH2:17][C@@H:12]([NH:11][C:9]([C:3]3[NH:4][C:5]([CH3:8])=[C:6]([Cl:7])[C:2]=3[Cl:1])=[O:10])[C@@H:13]([O:30][CH3:31])[CH2:14]2)[S:19][C:20]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N+:47]=[N-:48]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 68517894HCID 68517894, compound

Product 1

HCID 86643340HCID 86643340, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of ethyl 2-((3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-(hydroxymethyl)-1,3-thiazole-5-carboxylate (0.10 g, 0.2 mmol, Example 143) in anhydrous toluene was added diphenylphosphorylazide (0.053 mL, 0.24 mmol). The reaction was cooled to 0 deg and DBU was added slowly. After stirring at 0 deg for 30 min the reaction was warmed to room temperature and stirred overnight. The biphasic reaction mixture was washed with water (×3), 1NHCl (×1), brine (×1), dried with MgSO4 and concentrated (0.048 g). MS (ES) M+H: 516 for C19H23Cl2N7O4S.

Workup

  1. temperatureThe reaction was cooled to 0 deg
  2. stirringstirred overnight
  3. customThe biphasic reaction mixture
  4. washwas washed with water (×3), 1NHCl (×1), brine (×1)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated (0.048 g)

Sources & evidence

ORD record
ord-954a7ab558824e1ab602c986c859ec29
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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