Hydrochloric Acid → HCID 46897236, compound

HRID 1966966Notes

Reaction equation

HRID 1966966 reaction equation
C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[O:32]=[C:33]1[N:37]([CH2:38][C:39]([OH:41])=O)[C:36](=[O:42])[C:35]2([CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[N:34]1[C:48]1[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=1.[C:55]1([CH:61]([NH2:65])[CH2:62][CH2:63][CH3:64])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.Cl>CN1C(=O)CCC1>[O:32]=[C:33]1[N:37]([CH2:38][C:39]([NH:65][CH:61]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:62][CH2:63][CH3:64])=[O:41])[C:36](=[O:42])[C:35]2([CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)[N:34]1[C:48]1[CH:53]=[CH:52][C:51]([CH3:54])=[CH:50][CH:49]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 36037851-phenylbutan-1-amine2×HCID 66680556HCID 66680556, compound

Product 1

HCID 46897236HCID 46897236, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

170 μl (0.098 mmol, 0.1 eq.) of N,N-diisopropylethylamine and 204 mg (0.63 mmol, 2 eq.) of TBTU are added to a solution of 100 mg of (2,4-dioxo-1-p-tolyl-1,3-diazaspiro[4.5]dec-3-yl)acetic acid in 30 ml of NMP. The solution is stirred for 20 minutes, and 70 mg (0.47 mmol, 1.5 eq.) of 1-phenylbutylamine (starting material 3) are added. The reaction medium is stirred overnight at room temperature. It is then poured into 1N hydrochloric acid solution and extracted with ethyl acetate. The organic phase is then washed with water, then with 1N sodium hydroxide solution, and then again with water. It is dried over sodium sulfate. The residue is precipitated from dichloromethane and heptane. 2-(2,4-Dioxo-1-p-tolyl-1,3-diazaspiro[4.5]dec-3-yl)-N-(1-phenylbutyl)acetamide is obtained in the form of a white solid.

Workup

  1. stirringThe reaction medium is stirred overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is then washed with water
  4. dry with materialIt is dried over sodium sulfate
  5. customThe residue is precipitated from dichloromethane and heptane

Sources & evidence

ORD record
ord-5e277f2a924d49a2b2c3c94c58edaf87
Source dataset
uspto-grants-2013_04
Patent number
US08420681B2

Reaction notes

Loading…