Benzoylacetone → HCID 69835360, compound

HRID 2300653Notes

Reaction equation

HRID 2300653 reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[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>>[CH3:39]/[C:38](/[NH:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4])=[CH:37]/[C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 7166BenzoylacetoneHCID 69837796HCID 69837796, compound

Product 1

HCID 69835360HCID 69835360, 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 55 and 88 mg (0.54 mmol) of benzoylacetone to yield 142 mg (50% yield) of example 57: TLC (DCM/MeOH, 4/1): Rf=0.66; 1H NMR (DMSO-d6, 300 MHz) δ11.44 (d, 1H, J=9.0), 7.88-7.85 (m, 2H), 7.78-7.75 (m, 2H), 7.49-7.43 (m, 3H), 7.37-7.32 (m, 3H), 7.12 (d, 2H, J=8.4), 6.78 (d, 2H, J=8.4), 5.54 (s, 1H), 4.13 (m, 1H), 3.87 (t, 1H, J=6.0), 3.22-3.16 (m, 1H), 2.77 (d, 1H, J=14.4, 9.2), 2.56 (t, 2H, J=7.2), 2.22 (s, 3H), 2.00-1.93 (m, 2H), 1.66 (s, 3H); low resolution MS (ES+)m/e 525.15 (MH+).

Workup

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

Sources & evidence

ORD record
ord-1583642381234cd9a28fbf34aaefa656
Source dataset
uspto-grants-2002_12
Patent number
US06498174B1

Reaction notes

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