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

HRID 502394Notes

Reaction equation

HRID 502394 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:23]=[C:24](OCC)[C:25]=1[F:26])[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].C(OC1C=C(C=CC=1F)C=O)C.OC1C=C(C=CC=1F)C(O)=O.ClC1C=CC(C=O)=CC=1OCC.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[F:26])[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH:22]=[N:21][CH:20]=[N:19][CH:18]=2)=[O:16])[CH2:10][CH2:9]1)[CH3:2]

Participants

9

Reactant 6

HCID 81531DiisopropylethylamineHCID 5936354-Fluoro-3-hydroxybenzoic acidHCID 5003444Sodium cyanoborohydrideHCID 426142943-Ethoxy-4-fluorobenzaldehydeHCID 547756424-Chloro-3-ethoxybenzaldehydeHCID 68454648Pyrimidine-5-carboxylic acid[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-amide

Product 1

HCID 68457813Pyrimidine-5-carboxylic acid[1-(3-ethoxy-4-fluoro-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-fluoro-benzaldehyde [prepared from 3-hydroxy-4-fluoro-benzoic acid in analogy to the procedure described for the synthesis of 4-chloro-3-ethoxy-benzaldehyde in example 1a)], sodium cyano-borohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as light yellow solid. MS: 359.1 (MH+).

Sources & evidence

ORD record
ord-94ac3a2707ed4a9e9267ee91e7f03bcc
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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