Triethylamine → HCID 22254560, compound

HRID 1611704Notes

Reaction equation

HRID 1611704 reaction equation
[CH3:1][CH:2]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([NH2:19])[CH:15]=[CH:14]2)[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].CCN(CC)CC.[C:27]([O:35][CH2:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39](Cl)=[O:40])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C1C=CN=CC=1)C.C1COCC1>[C:27]([O:35][CH2:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39]([NH:19][C:16]1[CH:15]=[CH:14][C:13]2[C:18](=[C:9]([O:8][CH:2]([CH3:1])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH:10]=[CH:11][CH:12]=2)[N:17]=1)=[O:40])(=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 940042-((Benzoyloxy)methyl)benzoyl chlorideHCID 10083869HCID 10083869, compound

Product 1

HCID 22254560HCID 22254560, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 20 mL scintillation vial was added a stir bar, the title compound from Example 16 (100 mg, 0.388 mmol) and anhydr. THF (1.3 mL). To the resultant solution was added of Et3N (0.12 mL, 2.2 equiv), DMAP (5.0 mg, 1.06 equiv) and of 2-(benzoyloxymethyl)benzoyl chloride (116 mg, 1.1 equiv). The solution was stirred overnight, after which time the mixture was placed directly on a silica gel column and eluted with EtOAc/hexanes to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.23 (m, 1H), 8.16 (m, 1H), 7.92 (m, 2H), 7.72 (m, 1H), 7.55 (m, 4H), 7.38 (m, 4H), 7.24 (m, 1H), 5.51 (s, 2H), 4.82 (m, 1H), 1.88 (dd, 1H), 1.49 (dd, 1H), 1.34 (d, 3H), 0.92 (s, 9H); MS (DCI/NH3) m/z 497 [M+H]+.

Workup

  1. additionTo a 20 mL scintillation vial was added a stir bar
  2. washeluted with EtOAc/hexanes

Sources & evidence

ORD record
ord-3865804108a04420a03669c2b18264da
Source dataset
uspto-grants-2006_01
Patent number
US06989392B2

Reaction notes

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