Piperidine → HCID 23728790, compound

HRID 1944657Notes

Reaction equation

[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([C:19](O)=[O:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH:22]1[CH:23]=[CH:24]C2N(O)N=[N:28][C:26]=2[CH:27]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.N1CCCCC1>C1COCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([C:19]([N:28]4[CH2:24][CH2:23][CH2:22][CH2:27][CH2:26]4)=[O:20])[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-6-carboxylic acid (800 mg, 2.1 mmol) in THF (14 mL) was added HOBt (342 mg, 2.5 mmol), EDAC (807 mg, 4.2 mmol), triethylamine (1.7 g, 17 mmol) and piperidine (718 mg, 8.5 mmol) at room temperature. The reaction mixture was stirred at 40-50° C. for 12 h under a nitrogen atmosphere. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with a gradient of CH2Cl2/MeOH (100:1→50:1) to give the crude product, which was further purified by preparative HPLC to give 167 mg (21%) of [2-(4-isopropylpiperazin-1-yl)benzothiazol-6-yl]piperidin-1-ylmethanone as a trifluoroacetate salt.

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was purified by column chromatography on silica gel eluting with a gradient of CH2Cl2/MeOH (100:1→50:1)
customto give the crude product, which
customwas further purified by preparative HPLC

Sources & evidence

ORD record: ord-25f89eed6b774469b1b49743c85915fd
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394842B2

Reaction notes

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