Pyridine → HCID 57009313, compound

HRID 1955434Notes

Reaction equation

HRID 1955434 reaction equation
[CH3:1][C:2]([CH3:44])([CH3:43])[C@H:3]([NH:8][C:9](=[O:42])[C@@H:10]([CH2:18][C@@H:19]([OH:41])[CH2:20][S:21][C:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4](=[O:7])[NH:5][CH3:6].N1C=CC=CC=1.FC(F)(F)C(O)=O.Cl.CN(C)CCCN=C=NCC>CS(C)=O.CCOC(C)=O>[CH3:43][C:2]([CH3:1])([CH3:44])[C@H:3]([NH:8][C:9](=[O:42])[C@@H:10]([CH2:18][C:19](=[O:41])[CH2:20][S:21][C:22]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:4](=[O:7])[NH:5][CH3:6]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57197061HCID 57197061, compound

Product 1

HCID 57009313HCID 57009313, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.962 g (1.562 mmol) of the product of Example 33 in 3 mL of DMSO was added 0.505 mL (6.246 mmol) of pyridine followed by 0.120 mL (1.562 mmol) of trifluoroacetic acid and 0.898 (4.685 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The reaction mixture was stirred at room temperature for 36 h and then diluted with 200 mL of EtOAc. The resulting solution was washed with 0.1 N HCl solution, water, saturated NaHCO3 solution and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue, 0.948 g (99%) was used in the next step without purification. Electrospray Mass Spec: 615.4 (M+H)+.

Workup

  1. washThe resulting solution was washed with 0.1 N HCl solution, water, saturated NaHCO3 solution and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue, 0.948 g (99%) was used in the next step without purification

Sources & evidence

ORD record
ord-a1a3c05a73d547f899913e751cc3ef30
Source dataset
uspto-grants-2000_09
Patent number
US06124502

Reaction notes

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