Isopropanol → HCID 22969236, compound

HRID 2304350Notes

Reaction equation

HRID 2304350 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:13][C:14](=[O:35])[C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=[O:34])[C@H:21]([NH:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:22][CH:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.S(Cl)(Cl)=O.[CH3:40][CH:41](O)[CH3:42]>>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][NH:13][C:14](=[O:35])[C@@H:15]3[CH2:19][CH2:18][CH2:17][N:16]3[C:20](=[O:34])[C@H:21]([NH:29][CH2:30][C:31]([O:33][CH:41]([CH3:42])[CH3:40])=[O:32])[CH2:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 54248121HCID 54248121, compound

Product 1

HCID 22969236HCID 22969236, compound

Procedure

To a stirred solution of 96 mg of N-(1-amino-isoquinolin-6-ylmethyl) 1-(2-hydroxycarbonylmethylamino-2(R)-cyclohexylmethyl-acetyl)-prolinamide in 6 mL of 2-propanol was added 0.03 mL of thionyl chloride and the reaction mixture was heated at reflux temperature for two days. After this period the reaction mixture was concentrated, ethyl acetate added, washed with aqueous 5% sodium hydrogencarbonate and brine, dried over sodium sulphate and concentrated. The residue was dissolved in a t-butanol/water 1/1 (v/v) mixture lyophilisation yielded 56 mg of the title compound. MS ESI+: 524 (M+H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux temperature for two days
  3. concentrationAfter this period the reaction mixture was concentrated
  4. additionethyl acetate added
  5. washwashed with aqueous 5% sodium hydrogencarbonate and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in a t-butanol/water 1/1 (v/v) mixture lyophilisation

Sources & evidence

ORD record
ord-28db4023a32d49c6a174a00aaf6d84f5
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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