Acetic Anhydride → HCID 11361213, compound

HRID 1822918Notes

Reaction equation

HRID 1822918 reaction equation
[NH2:1][C:2]1[C:3]([C:8]2[CH:26]=[CH:25][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)=[O:13])=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>O1CCCC1>[C:27]([NH:1][C:2]1[C:3]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:17][CH:16]=3)=[O:13])=[CH:25][CH:26]=2)=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10382943HCID 10382943, compound

Product 1

HCID 11361213HCID 11361213, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 3 (150 mg, 0.435 mmol) in acetic anhydride (0.24 mL, 2.54 mmol) was heated in tetrahydrofuran (2 mL) at 40° C. overnight. The mixture was allowed to cool to room temperature and concentrated under reduced pressure to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.25 (s, 1H), 9.68 (s, 1H), 8.53 (dd, J=4.6 Hz, 1.5 Hz, 1H), 8.06 (m, 2H), 7.91 (dd, J=8.1 Hz, 1.3 Hz, 1H), 7.7–7.78 (m, 4H), 7.36–7.45 (m, 3H), 1.97 (s, 3H), 1.29 (s, 9H); MS (ESI30 ) m/z 388 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-98e5278c935f41b29a85094085df9685
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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