Pyrimidine-5-carboxylic acid → HCID 68456978, compound

HRID 502391Notes

Reaction equation

HRID 502391 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)=[O:9])[CH2:3][CH2:2]1.N1C=C(C(O)=O)C=NC=1.[C:25]([O:29][C:30](N1CCC(N)CC1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30]([N:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[CH:15]=[N:14][CH:13]=[N:12][CH:11]=2)=[O:9])[CH2:3][CH2:2]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 3

HCID 78346Pyrimidine-5-carboxylic acidHCID 12682914-Amino-1-Boc-piperidineHCID 68455584HCID 68455584, compound

Product 1

HCID 68456978HCID 68456978, compound

Procedure

In analogy to the procedure described in example 50k), pyrimidine-5-carboxylic acid piperidin-4-ylamide [prepared in analogy to the procedures described in examples 50 h) and 50i) by condensation of pyrimidine-5-carboxylic acid with 4-amino-piperidine-carboxylic acid tert-butyl ester to give 4-[(pyrimidine-5-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester followed by Boc cleavage with trifluoroacetic acid] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyano-borohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as light yellow solid. MS: 403.3 (MH+).

Workup

  1. customprepared in analogy to the procedures
  2. customdescribed in examples 50 h

Sources & evidence

ORD record
ord-1c3abb2f245c4450a0844618133bb875
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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