HCID 54413507, compound → HCID 54544963, compound

HRID 2399879Notes

Reaction equation

HRID 2399879 reaction equation
[OH:1][C@H:2]([CH2:27][O:28][C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([NH:36]C(=O)C)=[C:31]([Cl:40])[CH:30]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])=[CH:9][CH:8]=1>CO.Cl>[OH:1][C@H:2]([CH2:27][O:28][C:29]1[CH:34]=[C:33]([Cl:35])[C:32]([NH2:36])=[C:31]([Cl:40])[CH:30]=1)[CH2:3][NH:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])=[CH:11][CH:12]=1

Participants

4

Reactant 1

HCID 54413507HCID 54413507, compound

Product 1

HCID 54544963HCID 54544963, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 28 mg (0,016 mmol) of the acetamide from Example 208 in 5 mL of methanol and 0.24 mL of 2N aqueous hydrochloric acid was heated at reflux for 3 days. It was then cooled and concentrated. Purification by HPLC (ODS-3, 1:1 methanol:0.1% aqueous trifluoroacetic acid) gave 6.7 mg (13%) the title compound as its bis trifluoracetate salt: 1H NMR (400 MHz, CD3OD) δ8.31 (d, 1H, J=1.5 Hz), 7.96-7.90 (m, 3H), 7.75 (dd, 1H, J=1.9, 8.7 Hz), 7.65-7.57 (m, 2H), 7.11 (s, 4H), 6.89 (s, 2H), 4.12 (m, 1H), 3.89 (dd, 1H, J=5.0, 9.9 Hz), 3.85 (dd, 1H, J=5.3, 9.9 Hz), 3.23-3.11 (m, 4 HO, 2.90-2.86 (m, 2H).

Workup

  1. temperatureat reflux for 3 days
  2. temperatureIt was then cooled
  3. concentrationconcentrated
  4. customPurification by HPLC (ODS-3, 1:1 methanol:0.1% aqueous trifluoroacetic acid)

Sources & evidence

ORD record
ord-7112c66182cf4d87bc5ed7474bbd579c
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

Loading…