Triethylamine → 3-chloro-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

HRID 76869Notes

Reaction equation

HRID 76869 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[C:10]1(C(O)=O)[N:14]2[CH:15]=[N:16][CH:17]=[C:13]2[CH2:12][CH2:11]1.CCN(CC)CC>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[CH:10]1[N:14]2[CH:15]=[N:16][CH:17]=[C:13]2[CH2:12][CH2:11]1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58827078HCID 58827078, compound

Product 1

HCID 588270453-chloro-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 5-(2-chloro-4-cyanophenyl)-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole-5-carboxylic acid (0.02 g, 70 mol) is dissolved in DMSO (2 mL) and Et3N (0.2 mL) and heated at 100° C. for 2 h. The solution is evaporated to dryness and residue purified via reverse phase HPLC (5-100% MeCN/water w/0.1% TFA) to give 3-chloro-4-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-benzonitrile as a white solid. MS (ESI) m/z 244.2, 246.2 (M+H); 1H NMR (400 MHz, CDCl3) (TFA salt) δ ppm 2.60-2.73 (m, 1H), 3.08-3.20 (m, 2H), 3.22-3.36 (m, 1H), 6.04 (dd, J=7.6, 5.8 Hz, 1H), 6.91 (d, J=8.1 Hz, 1H), 7.24 (s, 1H), 7.61 (d, J=8.1 Hz, H), 7.81 (d, J=1.5 Hz, 1H), 8.53 (s, 1H).

Workup

  1. customThe solution is evaporated to dryness and residue
  2. custompurified via reverse phase HPLC (5-100% MeCN/water w/0.1% TFA)

Sources & evidence

ORD record
ord-7fa4dabdbddc4c8bac3fb4c220d5b9c3
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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