N-(2-Aminoethyl)piperidine → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-piperidine-1-yl-ethyl)-amide

HRID 1945481Notes

Reaction equation

HRID 1945481 reaction equation
[C:1]12([C:11]3[CH:30]=[CH:29][C:14]([O:15][CH2:16][C:17]4[O:18][C:19]5[CH:25]=[CH:24][C:23]([C:26](O)=[O:27])=[CH:22][C:20]=5[N:21]=4)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[N:31]1([CH2:37][CH2:38][NH2:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[N:31]1([CH2:37][CH2:38][NH:39][C:26]([C:23]2[CH:24]=[CH:25][C:19]3[O:18][C:17]([CH2:16][O:15][C:14]4[CH:13]=[CH:12][C:11]([C:1]56[CH2:10][CH:5]7[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]7)[CH2:8]5)[CH2:2]6)=[CH:30][CH:29]=4)=[N:21][C:20]=3[CH:22]=2)=[O:27])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 33944N-(2-Aminoethyl)piperidineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

Product 1

HCID 249672572-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-piperidine-1-yl-ethyl)-amideYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (70.2 mg, 0.17 mmol) and 2-piperidine-1-yl-ethylamine (0.049 ml, 0.35 mmol) in DMF 5.0 mL was added HBTU (132.7 mg, 0.35 mmol) and DIPEA (0.061 ml, 0.35 mmol). After stirring at room temperature, the mixture was partitioned between ethyl acetate and brine. The organic phase was dried (MgSO4 anh), and concentrated. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH=20:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid (2-piperidine-1-yl-ethyl)-amide as a white foam (18.9 mg, 22% yield).

Workup

  1. customthe mixture was partitioned between ethyl acetate and brine
  2. dry with materialThe organic phase was dried (MgSO4 anh)
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (CH2Cl2:MeOH=20:1)

Sources & evidence

ORD record
ord-993be1a0ba1d45218f215f987aaa69c3
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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