Triethylamine → HCID 67329693, compound

HRID 1673235Notes

Reaction equation

HRID 1673235 reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[N:7][C:8]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]=3[Cl:29])=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[CH:10]=2)[O:5][C:4]([CH3:31])([CH3:30])[CH2:3]1.[C:32](Cl)(=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34].CCN(CC)CC>C(Cl)Cl>[Cl:29][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:19]=1[C:8]1[N:7]=[C:6]2[O:5][C:4]([CH3:31])([CH3:30])[CH2:3][CH:2]([NH:1][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])[C:11]2=[CH:10][C:9]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 67023921HCID 67023921, compound

Product 1

HCID 67329693HCID 67329693, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step A (100 mg, 0.22 mmol) in 5.0 mL of CH2Cl2 was added pivaloyl chloride (32 μL, 0.26 mmol) and NEt3 (46 μL, 0.33 mmol). After stirring at rt for 16 h, the reaction mixture was concentrated. Chromatography on a Biotage 25+M cartridge using 1:1 v/v EtOAc/hexanes as the eluant afforded the product as a white solid.

Workup

  1. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a6889c1289ff4b7e8369472ef42c8a92
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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