Triethylamine → HCID 76582005, compound

HRID 735293Notes

Reaction equation

HRID 735293 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([CH3:25])([C:17]([NH:19][C:20]1[S:21][CH:22]=[CH:23][N:24]=1)=[O:18])[CH2:5]2.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH3:25][C:6]1([C:17]([NH:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[O:18])[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:3]=2)[CH:7]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 87668372HCID 87668372, compound

Product 1

HCID 76582005HCID 76582005, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 36 (11.3 mg, 0.032 mmol), Cu(OAc)2 (8.9 mg, 1.5 eq), phenylboronic acid (11.3 mg, 2.9 mmol), triethylamine (22.6 μL, 5 eq) and powdered 4 Å molecular sieve (33.7 mg) in CH2Cl2 (2.5 mL) was stirred at room temperature for 16 h while open to the atmosphere. After filtration to remove the molecular sieve, the filtrate was concentrated and purified by reverse-phase HPLC (80-100% solvent B gradient) to give Example 155. (4.9 mg, 36%). MS Found: (M+H)+=427.

Workup

  1. filtrationAfter filtration
  2. customto remove the molecular sieve
  3. concentrationthe filtrate was concentrated
  4. custompurified by reverse-phase HPLC (80-100% solvent B gradient)
  5. customto give Example 155

Sources & evidence

ORD record
ord-2722c919ea51459da87cd65b1d30c96a
Source dataset
uspto-grants-2009_09
Patent number
US07592461B2

Reaction notes

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