Isonicotinic Acid → HCID 57382893, compound

HRID 2168243Notes

Reaction equation

HRID 2168243 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C.Cl.[CH3:42][C:43]1[C:51]2[C:50]([N:52]3[CH2:57][CH2:56][CH:55]([NH2:58])[CH2:54][CH2:53]3)=[N:49][CH:48]=[N:47][C:46]=2[NH:45][CH:44]=1>CN(C)C=O>[CH3:42][C:43]1[C:51]2[C:50]([N:52]3[CH2:57][CH2:56][CH:55]([NH:58][C:7]([C:4]4[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=4)=[O:9])[CH2:54][CH2:53]3)=[N:49][CH:48]=[N:47][C:46]=2[NH:45][CH:44]=1

Participants

7

Reactant 5

HCID 5922Isonicotinic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86710200HCID 86710200, compound

Product 1

HCID 57382893HCID 57382893, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-pyridinecarboxylic acid (59.8 mg, 0.486 mmol), EDC.HCl (115 mg, 0.598 mmol), HOBt (92 mg, 0.598 mmol) and N,N-diisopropylethylamine (0.163 mL, 0.934 mmol) in N,N-dimethylformamide (1 mL), stirred for 10 minutes, was added 1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4-piperidinamine hydrochloride (100 mg), DU, and the reaction stirred for 18 h. The solvent was removed in vacuo and the mixture purified by high pH MDAP to give the title compound E27 (45 mg). 1H NMR (d6-DMSO) δ 11.53 (1H, s), 8.72 (2H, d), 8.66 (1H, d), 8.22 (1H, s), 7.78 (2H, d), 7.07 (1H, s), 4.09 (1H, m), 4.02 (2H, d), 3.06 (2H, t), 2.37 (3H, s), 1.95 (2H, d), 1.74 (2H, ddd), MS(ES+) 337 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe mixture purified by high pH

Sources & evidence

ORD record
ord-90a41dc8d61e468992cbb5cb61316ed9
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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