Ethylamine → N5-Ethyl-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-N4,N4-dimethyl-1,3-thiazole-4,5-dicarboxamide

HRID 2243028Notes

Reaction equation

HRID 2243028 reaction equation
[CH3:1][N:2]([CH3:25])[C:3]([C:5]1[N:6]=[C:7]([C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:18]=2)[S:8][C:9]=1[C:10]([OH:12])=O)=[O:4].C1C=C[C:29]2N(O)N=[N:32][C:30]=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl.C(N)C>CN(C)C=O.C(OCC)(=O)C>[CH2:30]([NH:32][C:10]([C:9]1[S:8][C:7]([C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]([NH:22][CH2:23][CH3:24])=[O:21])=[CH:17][CH:18]=2)=[N:6][C:5]=1[C:3]([N:2]([CH3:1])[CH3:25])=[O:4])=[O:12])[CH3:29]

Participants

8

Reactant 5

HCID 6341EthylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 592084804-[(Dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 59208457N5-Ethyl-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-N4,N4-dimethyl-1,3-thiazole-4,5-dicarboxamideYield 20%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-[(dimethylamino)carbonyl]-2-(6-{[(ethylamino)carbonyl]amino}pyridin-3-yl)-1,3-thiazole-5-carboxylic acid (Example 53, 0.12 g, 3.3 mmol) in dry dimethylformamide (2 mL), HOBT (0.101 g, 6.6 mmol), N-methylmorpholine (0.108 mL, 9.9 mmol), EDC hydrochloride (0.126 g, 6.6 mmol), ethylamine (2 M in tetrahydrofuran, 0.13 mL, 3.3 mmol) were added at 0° C. and stirred overnight at room temperature. After completion of the reaction, reaction mixture was diluted with ethyl acetate (20 mL) and was washed with water (1×20 mL), 2 N hydrochloric acid (1×20 mL), and sodium bicarbonate solution (1×20 mL). The organic layer was dried, concentrated under reduced pressure and the residue was triturated with acetonitrile (1 mL). The obtained solid was filtered and dried to afford 0.018 g (20%) of the title compound as white solid. MS (APCI): 391 (M+H+) for C18H23N5O3S; NMR: δ 1.06 (t, 3H), 2.86 (s, 3H), 2.99 (s, 3H), 3.17 (q, 4H), 7.60 (d, 1H), 7.76 (br s, 1H), 8.22 (dd, 1H), 8.72 (br t, 1H), 8.78 (s, 1H), 9.52 (br s, 1H).

Workup

  1. customAfter completion of the reaction, reaction mixture
  2. washwas washed with water (1×20 mL), 2 N hydrochloric acid (1×20 mL), and sodium bicarbonate solution (1×20 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was triturated with acetonitrile (1 mL)
  6. filtrationThe obtained solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-13ad2c0aae0349e599015cdf789f633a
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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