Acetate → HCID 22175538, compound

HRID 1797689Notes

Reaction equation

[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[S:17][C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:21])[N:20]=3)[CH:14]=2)[C:9](=[O:27])[N:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:7]=1[CH2:32][NH:33]C(OC(C)(C)C)=O)[CH2:2][CH2:3][CH3:4].C([O-])(=O)C.[ClH:45]>>[ClH:45].[NH2:33][CH2:32][C:7]1[N:8]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:9](=[O:27])[C:10]2[C:15]([C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][C:13]([C:16]1[S:17][C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:21])[N:20]=1)=[CH:12][CH:11]=2

Participants

Reactant 3

HCID 175Acetate

HCID 313Hydrochloric Acid

HCID 22175509HCID 22175509, compound

Product 1

HCID 22175538HCID 22175538, compoundYield 93.3%

Procedure

Ethyl 2-(4-butoxy-3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl)-4-methyl-1,3-thiazole-5-carboxylate (0.17 g, 0.3 mmol) was dissolved in a solution of 4N hydrogen chloride in ethyl; acetate (5 ml). The solution was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate to give ethyl 2-[3-(aminomethyl)-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinyl]-4-methyl-1,3-thiazole-5-carboxylate hydrochloride (0.14 g, 93.3%) as crystals.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record: ord-917d6779458248d8863b580b00c2ddd4
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034039B2

Reaction notes

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