4-Methylmorpholine → HCID 56848568, compound

HRID 1470348Notes

Reaction equation

HRID 1470348 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](O)=[O:26])[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C[N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[O:35]1[CH2:36][CH2:37][N:32]([C:25]([C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]4[CH:14]=[C:13]([C:5]5[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=5)[O:21][C:20]=34)[CH:23]=2)=[O:26])[CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 79724-MethylmorpholineHCID 66779501HCID 66779501, compound

Product 1

HCID 56848568HCID 56848568, compoundYield 70%

Procedure

Starting from 3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzoic acid (0.062 mmol) and 4-methylmorpholin (0.182 mmol) the product is prepared analogously to “A43” and obtained as colorless solid in a yield of 70%. HPLC (method A): Rt 2.59 min (purity 98.1%); LCMS (ESI+) (method E): Rt 1.76 min, M+H+ 475.2 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.58 (d, J=5.1, 1H), 8.29 (t, J=1.5, 1H), 8.19 (d, J=8.0, 1H), 7.76 (s, 1H), 7.74-7.65 (m, 2H), 7.58 (d, J=7.6, 1H), 7.33 (s, 2H), 3.91 (d, J=11.4, 6H), 3.74 (s, 3H), 3.69-3.37 (m, 8H).

Workup

  1. customis prepared analogously to “A43”
  2. customobtained as colorless solid in a yield of 70%

Sources & evidence

ORD record
ord-a8d8823f19c24d2dade8ffc54777ded5
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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