Benzoylacetone → HCID 69835532, compound

HRID 2300652Notes

Reaction equation

HRID 2300652 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[N:17]=[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:19][C:20]=2[CH2:21][CH3:22])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].[C:29]([CH2:37][C:38](=O)[CH3:39])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:21]([C:20]1[O:19][C:18]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:17][C:16]=1[CH2:15][CH2:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C@H:2]([NH:1]/[C:38](/[CH3:39])=[CH:37]\[C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:3]([OH:5])=[O:4])=[CH:8][CH:9]=1)[CH3:22]

Participants

3

Reactant 2

HCID 7166BenzoylacetoneHCID 18343038HCID 18343038, compound

Product 1

HCID 69835532HCID 69835532, compound

Procedure

The title compound was prepared (as described above for the preparation of example 1) from a suspension of 205 mg (0.54 mmol) of Intermediate 52 and 87 mg (0.54 mmol) of benzoylacetone to yield 145 mg (51%) of example 55: TLC (DCM/MeOH, 4/1): Rf=0.60; 1H NMR (DMSO-d6, 300 MHz) δ11.42 (d, 1H, J=9.0), 7.89-7.86 (m, 2H), 7.77-7.74 (m, 2H), 7.48-7.32 (m, 6H), 7.11 (d, 2H, J=8.4), 6.77 (d, 2H, J=8.4), 5.53 (s, 1H), 4.1 (t, 1H, J=6.3), 3.2-3.14 (m, 2H), 2.86 (t, 2H, J=6.3), 2.79-2.74 (m, 1H), 2.67 (q, 2H, J=7.5), 1.65 (s, 3H), 1.17 (t, 3H, J=7.5); low resolution MS (ES+)m/e 525.2 (MH+).

Workup

  1. customas described above for the preparation of example 1)

Sources & evidence

ORD record
ord-a811dcc7adeb4638a425f57dd29ba146
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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