Triethylamine → HCID 16124215, compound

HRID 730659Notes

Reaction equation

HRID 730659 reaction equation
[CH3:1][C:2]1([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:14]=[C:15]1[N:21]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C@@H:31]([C:42](O)=[O:43])[CH2:32][C:33]3[CH:38]=[C:37]([CH3:39])[C:36]([OH:40])=[C:35]([CH3:41])[CH:34]=3)=[O:29])[CH2:24][CH2:23]2)[CH2:20][CH2:19][C:18]2[CH:45]=[CH:46][CH:47]=[CH:48][C:17]=2[NH:16]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:14]=[C:15]1[N:21]([CH:22]2[CH2:23][CH2:24][N:25]([C:28]([O:30][C@H:31]([CH2:32][C:33]3[CH:34]=[C:35]([CH3:41])[C:36]([OH:40])=[C:37]([CH3:39])[CH:38]=3)[C:42]([N:5]3[CH2:6][CH2:7][C:2]([CH3:1])([N:8]4[CH2:9][CH2:10][O:11][CH2:12][CH2:13]4)[CH2:3][CH2:4]3)=[O:43])=[O:29])[CH2:26][CH2:27]2)[CH2:20][CH2:19][C:18]2[CH:45]=[CH:46][CH:47]=[CH:48][C:17]=2[NH:16]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 12410239342412-40-2HCID 67273812HCID 67273812, compound

Product 1

HCID 16124215HCID 16124215, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

55 mg (0.22 mmol) 4-(4-methyl-piperidin-4-yl)-morpholine (used as the hydrochloride salt, purity 90%) were added at RT to a solution of 90 mg (0.19 mmol) (R)-2-(4-hydroxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1h), 70 mg (0.22 mmol) TBTU and 70 μL (0.50 mmol) triethylamine in 1 mL DMF and the reaction mixture was stirred for 20 h. The reaction solution was poured onto saturated NaHCO3 solution, the precipitate formed was filtered off and dried. Further purification was carried out by HPLC, the fractions containing the product were combined and lyophilised.

Workup

  1. customthe precipitate formed
  2. filtrationwas filtered off
  3. customdried
  4. customFurther purification
  5. additionthe fractions containing the product

Sources & evidence

ORD record
ord-5d6f72b20db647c4beab4697563b118f
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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