Diisopropylethylamine → Pyrimidine-5-carboxylic acid[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amide

HRID 502393Notes

Reaction equation

HRID 502393 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:23]=[C:24](OCC)[C:25]=1F)[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:18]=[N:19][CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:10][CH2:9]1)[CH3:2].[CH2:30]([O:32]C1C=C(C=CC=1OC)C=O)C.C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[O:32][CH3:30])[CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([C:17]2[CH:18]=[N:19][CH:20]=[N:21][CH:22]=2)=[O:16])[CH2:12][CH2:13]1)[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2447283-Ethoxy-4-methoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68454648Pyrimidine-5-carboxylic acid[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-amide

Product 1

HCID 68456362Pyrimidine-5-carboxylic acid[1-(3-ethoxy-4-methoxy-benzyl)-piperidin-4-yl]-amide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), pyrimidine-5-carboxylic acid piperidin-4-ylamide (example 56) was reacted with 3-ethoxy-4-methoxy-benzaldehyde, sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 371.1 (MH+).

Sources & evidence

ORD record
ord-fe93eb431be4452e9ff298a45990645c
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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