Ethylamine → N-Ethyl-5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinamide

HRID 1878597Notes

Reaction equation

HRID 1878597 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[N:9]=[C:10]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([CH:25]=3)[C:22](O)=[O:23])[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:26]([NH2:28])[CH3:27].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CC#N>[CH2:26]([NH:28][C:22](=[O:23])[C:21]1[CH:25]=[C:17]([C:10]2[C:11]3[CH:16]=[CH:15][NH:14][C:12]=3[N:13]=[C:8]([C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[N:9]=2)[CH:18]=[N:19][CH:20]=1)[CH3:27]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 687615905-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinic acid2×

Product 1

HCID 44194351N-Ethyl-5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-[2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-nicotinic acid (Intermediate 5) (1 eq, 0.143 mmol, 50 mg) in MeCN (3 ml), ethylamine (1 eq, 0.143 mmol, 6.6 mg), EDC hydrochloride (1.5 eq, 0.215 mmol, 42 mg), HOBt (1.2 eq, 0.172 mmol, 23 mg), and TEA (5 eq, 0.720 mmol, 0.1 ml) are added. The mixture is heated using microwave radiation at 140° C. for 20 min. The resulting precipitate is filtered off and washed with MeCN. Drying the solid in vacuum affords the title compound; [M+H]+=359; 1H-NMR (400 MHz, CD3OD): δ 9.55 (d, 1H), 9.15 (t, 1H), 9.12 (d, 1H), 8.47 (d, 1H), 7.86 (t, 1H), 7.67 (d, 1H), 7.36 (d, 1H), 6.99 (d, 1H), 3.50 (q, 2H), 2.68 (s, 3H), 1.29 (t, 3H).

Workup

  1. temperatureThe mixture is heated
  2. customat 140° C.
  3. customfor 20 min
  4. filtrationThe resulting precipitate is filtered off
  5. washwashed with MeCN
  6. customDrying the solid in vacuum

Sources & evidence

ORD record
ord-43286868491e4a4499317fd74e48ca52
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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