Ethanolamine → HCID 67400675, compound

HRID 913143Notes

Reaction equation

[Cl:1][C:2]1[C:24]([O:25][CH2:26][CH3:27])=[CH:23][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][N:15]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:28][CH2:29][CH3:30].[NH2:31][CH2:32][CH2:33][OH:34].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[C:24]([O:25][CH2:26][CH3:27])=[CH:23][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([NH:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:31][CH2:32][CH2:33][OH:34])=[O:20])=[CH:16][N:15]=3)[CH2:11][CH2:12]2)=[CH:4][C:3]=1[O:28][CH2:29][CH3:30]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 6-[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-ylamino]-nicotinic acid (65.09 mg, 0.15 mmol, 1.0 equiv; example 70) and 2-amino-ethanol (46.4 mg, 0.25 mmol, 1.67 equiv; commercially available) in dry DMF (2.0 mL) and N-ethyl diisopropylamine (0.3 mL) was added HATU (68.44 mg, 0.18 mmol, 1.2 quiv; commercially available) and the reaction stirred at 60° 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 30.1 mg (42%) of the title compound. MS (ISP): 477.3 [M+H]+.

Workup

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-abe7ffc45c7b4349ada5b5db595ec51e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026255B2

Reaction notes

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