2-Pyridinecarboxaldehyde → HCID 59468437, compound

HRID 1716397Notes

Reaction equation

HRID 1716397 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)[N:8]=2)=[CH:4][CH:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=O>CC(O)=O.CC(N(C)C)=O>[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 59468418HCID 59468418, compound

Product 1

HCID 59468437HCID 59468437, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of [4-(5-aminothiophen-2-yl)-pyrimidin-2-yl]-m-tolyl-amine (prepared according to Method 4) (15 mg, 0.053 mmol) and pyridine-2-carbaldehyde (4.5 uL, 0.048 mmol) were dissolved in a 25% solution of HOAc in DMA (0.5 mL). MP-CNBH3 resin (2.5 eq.) was added after 2 h and the reaction was shaken for 18 h. The reaction was filtered and the resin washed with DMA. The crude mixture was purified by preparative LCMS to afford 11.1 mg, 61.2%). MS: m/z 374 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ2.26 (s, 3H), 4.42 (d, J=6.5 Hz, 2H), 5.96 (d, J=4.5 Hz, 1H), 6.72 (d, J=7.5 Hz, 1H), 6.986 (d, J=5.5 Hz, 1H), 7.10 (t, J=7.5 Hz, 1H), 7.27 (m, 1H), 7.38 (d, J=7.5 Hz, 1H), 7.47 (d, J=7.5 Hz, 1H), 7.56 (d, J=4.0 Hz, 1H), 7.73 (br s, 1H), 7.76 (m, 1H), 7.81 (t, J=5.5 Hz, 1H), 8.16 (d, J=6.0 Hz, 1H), 8.53 (br dd, J=4.5 Hz, 1H), 9.24 (s, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. washthe resin washed with DMA
  3. customThe crude mixture was purified by preparative LCMS
  4. customto afford 11.1 mg, 61.2%)

Sources & evidence

ORD record
ord-e2225d5b78ce4b0e825f91a2ad8971bd
Source dataset
uspto-grants-2010_09
Patent number
US07803806B2

Reaction notes

Loading…