Isopropanol → HCID 22969236, compound

HRID 1279129Notes

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

Reactant 3

HCID 3776Isopropanol

HCID 24386Thionyl Chloride

HCID 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 6mL of 2-propanol was added 0.03 mL of thionyl chloride and the reaction mixture was heated at refux 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

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

Sources & evidence

ORD record: ord-40c3367686554899b334794240e390e6
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444672B1

Reaction notes

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