Potassium Carbonate → HCID 178420491, compound

HRID 45944Notes

Reaction equation

HRID 45944 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[NH:3][CH:2]=1.Br[CH2:12][C:13]1[C:23]2[O:22][CH2:21][CH2:20][CH2:19][O:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.[C:24]([O-:27])([O-])=O.[K+].[K+]>>[O:22]1[CH2:21][CH2:20][CH2:19][O:18][C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:12][N:10]([CH2:12][C:13]3[C:23]4[O:22][CH2:21][CH2:20][CH2:19][O:27][C:24]=4[CH:16]=[CH:15][CH:14]=3)[C:8]3[CH:7]=[CH:6][C:5]4[NH:1][CH:2]=[N:3][C:4]=4[CH:9]=3)[C:23]1=2

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 136235-AminobenzimidazoleHCID 27949926-(bromomethyl)-3,4-dihydro-2H-1,5-benzodioxepine

Product 1

HCID 178420491HCID 178420491, compound

Procedure

The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), 6-(bromomethyl)-3,4-dihydro-1,5-benzodioxepin (535 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.098 g (21.4%); MS m/z: 458.5 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 2.10 (quin, 4H, 3J=5.5 Hz); 4.10 (t, 4H, 3J=5.5 Hz); 4.15 (t, 4H, 3J=5.5 Hz); 4.61 (s, 4H); 6.58-6.60 (m, 2H); 6.76-6.85 (m, 6H); 7.31 (d, 1H, 3J=9.8 Hz); 7.88 (s, 1H); 11.89 (br s, 1H); HPLC (METHOD [A]): rt 16.11 min (92.3%)

Workup

  1. customThe compound was synthesized
  2. customrt 16.11 min (92.3%)

Sources & evidence

ORD record
ord-4955fa7c986c45238d0d64be0d0389cc
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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