Water → HCID 68084481, compound

HRID 1470344Notes

Reaction equation

HRID 1470344 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=O)[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].CN1CCOCC1.[NH2:38][CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1[NH2:45].O>CN(C)C=O>[NH2:38][CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1[NH:45][C:25](=[O:27])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:14]=[C:13]([C:5]4[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=4)[O:21][C:20]=23)[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 46101,2-DiaminocyclohexaneHCID 79724-MethylmorpholineHCID 66779501HCID 66779501, compound

Product 1

HCID 68084481HCID 68084481, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-[2-(3,4,5-Trimethoxy-phenyl)-furo[3,2-b]pyridin-7-yl]-benzoic acid (0.049 mmol) is dissolved in N,N-dimethylformamid (1.00 ml) and N-(3-dimethyl-aminopropyl)-N′-ethylcarbodiimidhydrochloride (0.110 mmol), 1-hydroxybenzotriazolhydrat (0.111 mmol), 4-Methylmorpholin (0.146 mmol) and 1,2-Diaminocyclohexane (0.049 mmol) are added. The reaction solution is stirred 2 d at RT. Water is added and the solvent removed in vacuo. The product is isolated after column reversed phase column chromatography as yellow solid in a yield of 27%. HPLC (method A): Rt 2.47 min (purity 100%); LCMS (ESI+) (method E): Rt 1.69 min, M+H+ 502.2 m/z.

Workup

  1. customthe solvent removed in vacuo
  2. customThe product is isolated after column

Sources & evidence

ORD record
ord-87513f1e87f74d378f9fd9d46486dd42
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

Loading…