1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86653427, compound

HRID 1874069Notes

Reaction equation

HRID 1874069 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1.C1CCN2C(=NCCC2)CC1.N1([C:28](=[O:33])[CH2:29][CH2:30][O:31][CH3:32])C=CN=C1>C(#N)C>[CH3:32][O:31][CH2:30][CH2:29][C:28]([NH:1][C:2]1[S:3][C:4]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:5]=2[N:6]=1)=[O:33]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5878502-Amino-4,5,6,7-tetrahydro-1,3-benzothiazol-7-oneHCID 58939129HCID 58939129, compound

Product 1

HCID 86653427HCID 86653427, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 2-amino-5,6-dihydro-4H-benzothiazol-7-one (3.0 g, 18 mmol) and DBU (5.3 mL, 36 mmol) in 100 mL acetonitrile is added a solution of 1-imidazol-1-yl-3-methoxy-propan-1-one (6.9 g, 45 mmol) in acetonitrile. The reaction mixture is stirred for 15 min at RT and then concentrated under reduced pressure. The residue is poured in water, acidified to pH 5 with 6 M aqueous HCl and the product is extracted with ethyl acetate. The combined organic phases are dried over MgSO4 and concentrated under reduced pressure. Yield: 3.8 g. The product is used in the next step without purification. A-36 is synthesized according to general procedure A1 starting from 3.8 g (15 mmol) A-36c and 6.8 g (24 mmol) A-36b. Yield: 1.23 g.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue is poured in water
  3. extractionthe product is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product is used in the next step without purification
  7. customA-36 is synthesized

Sources & evidence

ORD record
ord-3d65da1a088148618f6b942e89cfbc21
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

Loading…