4-Aminopyridine → HCID 25182750, compound

HRID 1746698Notes

Reaction equation

HRID 1746698 reaction equation
[CH:1]1([NH:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1>>[CH:1]1([NH:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 2

HCID 17274-AminopyridineHCID 594470756-(Cyclohexylamino)pyrimidine-4-carboxylic acid2×

Product 1

HCID 25182750HCID 25182750, compound

Procedure

Following the general method as outlined in Example 1, starting from 6-(cyclohexylamino)pyrimidine-4-carboxylic acid (Intermediate 4) and 4-aminopyridine (Aldrich), the title compound was obtained as a yellow solid after purification by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc. 1H NMR (300MHz, DMSO-d6) δ [ppm] 10.82 (1H, s), 8.56 (1H, s), 8.47 (2H, d, J=5.0 Hz), 7.89 (2H, d, J=5.0 Hz), 7.84 (1H, d, J=9.0 Hz), 7.16 (1H, s), 3.88 (1H, m), 1.91-1.57 (5H, m), 1.39-1.16 (5H, m). MS (ESI): 298.0. HPLC (Condition A): Rt 2.12 min (HPLC purity 99.4%).

Sources & evidence

ORD record
ord-311e2900898f41999723960a3cf82a63
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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