Triethylamine → HCID 10174570, compound

HRID 1610994Notes

Reaction equation

HRID 1610994 reaction equation
C([NH:4][CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[C:10]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Cl:32])[C:6]([OH:8])=[O:7])(=O)C.C(N(CC)CC)C.C1C=NC2N(O)N=NC=2C=1.[F:50][CH:51]([F:55])[C:52](O)=[O:53].CCN=C=NCCCN(C)C>C(Cl)Cl.CCOC(C)=O>[Cl:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][C:10]1[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:12][CH:13]=[CH:14][C:9]=1[CH:5]([NH:4][C:52](=[O:53])[CH:51]([F:55])[F:50])[C:6]([OH:8])=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 10151939HCID 10151939, compound

Product 1

HCID 10174570HCID 10174570, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Example 13 Part A compound (222 mg, 0.45 mmol) under argon at room temperature in CH2Cl2 (2.5 mL) was added triethylamine (85 μL, 0.6 mmol), HOAt (69 mg, 0.5 mmol) and difluoroacetic acid (48 mg, 0.5 mmol) was added EDAC (96 mg, 0.5 mmol). After 16 h, the reaction mixture was diluted with EtOAc, washed once with 10% citric acid, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 156 mg (64% yield). LC/MS gave the correct molecular ion [(M+H)+=538] for the desired compound.

Workup

  1. washwashed once with 10% citric acid
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-04c91fa03c6a4c6b811ba95590ff410e
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

Loading…