Acetic Acid → Benzothiazol-2-yl-[1-(2-ethoxy-naphthalen-1-ylmethyl)-piperidin-4-yl]-amine

HRID 1990796

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[CH2:17]([O:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]=1[CH:30]=O)[CH3:18].C(N(C(C)C)CC)(C)C.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:30][C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:28]=[CH:29][C:20]=2[O:19][CH2:17][CH3:18])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of benzothiazol-2-yl-piperidin-4-yl-amine (23.3 mg, 0.1 mmol, 1.0 equiv) and 2-ethoxy-naphthalene-1-carbaldehyde (commercially available, 24.0 mg, 0.12 mmol, 1.2 equiv) in ethanol (2 mL) was added diisopropylethylamine (23.42 μL, 25.9 mg, 0.2 mmol, 2.0 equiv) and acetic acid (18.0 mg, 0.3 mmol, 3.0 equiv) and the mixture stirred at 40° C. After 1 h, sodium cyano borohydride (7.54 mg, 0.12 mmol, 1.2 equiv) was added and the mixture stirred at 40° C. over night. Removal of the solvent under reduced pressure and purification by preparative HPLC on reversed phase eluting with a gradient of acetonitrile/water provided 3.3 mg (8%) of the title compound. MS (ESI): 418.4 [M+H]+.

Workup

stirringthe mixture stirred at 40° C. over night
customRemoval of the solvent
customunder reduced pressure and purification by preparative HPLC on reversed phase
washeluting with a gradient of acetonitrile/water

Sources & evidence

ORD record: ord-8ee5054967184bad9481d5be680ac808
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645753B2

Linked notes

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