Triethylamine → (3S)-3-methyl-4-(((2S)-4-(1,3-thiazol-2-ylsulfonyl)-2-piperazinyl)methyl)morpholine

HRID 1972478Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[CH2:8][C@H:9]1[CH2:14][N:13]([S:15]([C:18]2[S:19][CH:20]=[CH:21]C=2)(=[O:17])=[O:16])[CH2:12][CH2:11][NH:10]1.C([N:25](CC)CC)C.S1C=CN=C1S(Cl)(=O)=O>C(Cl)Cl>[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][N:3]1[CH2:8][C@H:9]1[CH2:14][N:13]([S:15]([C:18]2[S:19][CH:20]=[CH:21][N:25]=2)(=[O:16])=[O:17])[CH2:12][CH2:11][NH:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

A 50-mL round-bottomed flask was cooled to 0° C. and charged with (3S)-3-methyl-4-((2R)-2-piperazinylmethyl)morpholine (100 mg, 0.5 mmol, Example 82, Step 2), CH2Cl2 (5 mL) and triethylamine (0.07 mL, 0.5 mmol). Thiazole-2-sulfonyl chloride (92 mg, 0.5 mmol, Bioorg. Med. Chem., 2006, 14, 6628) was added and after 10 min the reaction was concentrated and acidified with 4 N HCl in dioxane (5 mL). The HCl salt was collected after filtration and the crude material was purified via column chromatography (40 g silica gel, 0 to 10% (2M NH3 in MeOH) in CH2Cl2) to give (3S)-3-methyl-4-(((2S)-4-(1,3-thiazol-2-ylsulfonyl)-2-piperazinyl)methyl)morpholine (210 mg).

Workup

concentrationwas concentrated
customThe HCl salt was collected
filtrationafter filtration
customthe crude material was purified via column chromatography (40 g silica gel, 0 to 10% (2M NH3 in MeOH) in CH2Cl2)

Sources & evidence

ORD record: ord-27e431ee0c6b4edca5ce124316ab31e6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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