N,N-Dimethyl-1,3-propanediamine → HCID 66779476, compound

HRID 1470347Notes

Reaction equation

HRID 1470347 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].[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][NH2:36]>>[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35][NH:36][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:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[O:21][C:20]=23)[CH:23]=1

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 66779501HCID 66779501, compound

Product 1

HCID 66779476HCID 66779476, compoundYield 33%

Procedure

Starting from 3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzoic acid (0.062 mmol) and N,N-dimethyltrimethylendiamin (0.064 mmol) the product is prepared analogously to “A43” and obtained as yellow solid in a yield of 33%. HPLC (method A): Rt 2.45 min (purity 99.3%); LCMS (ESI+) (method E): Rt 1.56 min, M+H+ 490.3 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.82 (s, 1H), 8.77-8.68 (m, 1H), 8.60 (d, J=5.1, 1H), 8.27 (d, J=7.8, 1H), 8.01 (d, J=7.8, 1H), 7.78 (s, 1H), 7.77-7.69 (m, 2H), 7.37 (s, 2H), 3.93 (s, 6H), 3.74 (s, 3H), 3.49-3.18 (m, 2H), 2.45-2.10 (m, 8H), 1.78-1.63 (m, 2H).

Workup

  1. customis prepared analogously to “A43”
  2. customobtained as yellow solid in a yield of 33%

Sources & evidence

ORD record
ord-7d3fc450a7014bf2b7e2bd3ba8902dd9
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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