Triethylamine → HCID 57742603, compound

HRID 1806136Notes

Reaction equation

HRID 1806136 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19](O)=[O:20])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.Cl.C[N:27](C)CCCN=C=NCC.[NH4+].[Cl-].C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([S:15][C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([NH2:27])=[O:20])[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 57742950HCID 57742950, compound

Product 1

HCID 57742603HCID 57742603, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(5-bromo-2-(4-methylthiazol-2-ylamino)pyridin-3-ylthio)benzoic acid (0.35 g, 0.83 mmol) was dissolved in DMF (5 mL). 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.24 g, 1.2 mmol), NH4Cl (0.133 g, 2.5 mmol) and HOBT-H2O (0.19 g, 1.2 mmol) were added. Triethylamine (0.29 mL, 2.1 mmol) was added last. The reaction stirred at room temperature overnight. The material was diluted with water and the solid was filtered to give the title compound (0.23 g, 67% yield). 1H NMR (DMSO-d6) δ 2.17 (s, 3H), 6.40 (bs, 1H), 7.48 (s, 1H), 7.53-7.56 (m, 2H), 7.90-7.96 (m, 2H), 8.08 (s, 1H), 8.27 (bs, 1H).

Workup

  1. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-31f84cdcaeac4c62b7351981348c15f3
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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