3-Aminopyridine → HCID 71620846, compound

HRID 2174232Notes

Reaction equation

HRID 2174232 reaction equation
Cl.C(N=C=NCCCN(C)C)C.O.O[N:15]1[C:19]2C=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=N1.[CH2:24]([NH:26][C:27](=[O:45])[NH:28][C:29]1[N:34]=[C:33]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:32]([C:42]([OH:44])=O)=[CH:31][N:30]=1)[CH3:25].NC1C=NC=CC=1>CN(C)C=O.O>[CH2:24]([NH:26][C:27](=[O:45])[NH:28][C:29]1[N:34]=[C:33]([NH:35][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:32]([C:42]([NH:17][C:18]2[CH:19]=[N:15][CH:21]=[CH:22][CH:23]=2)=[O:44])=[CH:31][N:30]=1)[CH3:25]

Participants

7

Reactant 4

HCID 100093-AminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 89650866HCID 89650866, compound

Product 1

HCID 71620846HCID 71620846, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.096 g, 0.500 mmol) and 1-hydroxybenzotriazole monohydrate (0.077 g, 0.500 mmol) were added to a stirred solution of 2-(3-ethylureido)-4-(phenylamino)pyrimidine-5-carboxylic acid (v) (0.100 g, 0.330 mmol) in dimethylformamide (3 mL) at room temperature. After 15 min, 3-aminopyridine (0.047 g, 0.500 mmol) was added and the reaction mixture stirred at 40° C. for 24 h. The mixture was cooled to room temperature, treated with water (2 mL) and the resulting off-white precipitate filtered, washed with water, air-dried and triturated with hot EtOH to give Compound 6 (0.060 g, 0.159 mmol, 48%) as a colourless powder. 1H NMR (300 MHz, DMSO-d6): δ 10.67 (1H, br s), 10.52 (1H, br s), 9.89 (1H, br s), 8.91-8.84 (3H, m), 8.35 (1H, dd, J 1.0 and 4.6), 8.12 (1H, dt, J 2.0 and 8.7), 7.67 (2H, d, J 8.2), 7.46-7.38 (3H, m), 7.20 (1H, t, J 7.2), 3.10 (2H, dq, J 5.6 and 7.2), 0.93 (3H, t, J 7.2); [M+H]+ m/z=378.2.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe resulting off-white precipitate filtered
  3. washwashed with water
  4. customair-dried
  5. customtriturated with hot EtOH

Sources & evidence

ORD record
ord-29e255b839f54f4481e1efd316d83e20
Source dataset
uspto-grants-2015_06
Patent number
US09060515B2

Reaction notes

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