Hydrochloric Acid → HCID 86694215, compound

HRID 707359Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][N:23]=[C:18]3[C:17]([CH3:25])([CH3:24])[C:16]2=[O:26])[CH2:11]1.[CH3:27]C1(C)C2C(=NC=CN=2)N([C@@H]2CCN(C(OC(C)(C)C)=O)C2)C1=O.[ClH:51].O1CCOCC1>>[CH:19]([N:15]([CH:12]([CH3:11])[CH3:13])[CH2:16][CH3:17])([CH3:18])[CH3:27].[Cl:51][C:2]1[S:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1.[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:14][CH2:13][C@@H:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][N:23]=[C:18]3[C:17]([CH3:24])([CH3:25])[C:16]2=[O:26])[CH2:11]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 86694216HCID 86694216, compound

HCID 86694217HCID 86694217, compound

Product 3

HCID 119872-Chlorobenzothiazole

HCID 81531Diisopropylethylamine

HCID 86694215HCID 86694215, compoundYield 60.9%

Procedure

The title compound was synthesized following the procedure described for (S)-5-(1-(benzo[d]thiazol-2-yl)pyrrolidin-3-yl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (See EXAMPLE 141), using (R)-tert-butyl 3-(7,7-dimethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-b]pyrazin-5-yl)pyrrolidine-1-carboxylate (0.3 g, 0.903 mmol), hydrogen chloride, 4M in 1,4-dioxane (10 mL, 40.0 mmol), diisopropylethylamine (1 mL, 5.75 mmol), and 2-chlorobenzothiazole (0.153 mL, 0.903 mmol) to afford (R)-5-(1-(benzo[d]thiazol-2-yl)pyrrolidin-3-yl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.201 g, 0.550 mmol, 60.9% yield). m/z: 366.0 (M+1);

Workup

customThe title compound was synthesized

Sources & evidence

ORD record: ord-81a93de160a146de8f7d3a37fb97221f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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