Ammonia → HCID 86693511, compound

HRID 575449Notes

Reaction equation

HRID 575449 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:30]3[CH2:31][CH:28]([CH2:29]3)[C:8]3[N:9]([CH2:17][C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([CH3:27])[N:19]=4)[C:10]([C:12]([O:14]CC)=O)=[N:11][C:7]=3[C:6]=2[CH:32]=1.[NH3:33]>>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:30]3[CH2:31][CH:28]([CH2:29]3)[C:8]3[N:9]([CH2:17][C:18]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([CH3:27])[N:19]=4)[C:10]([C:12]([NH2:33])=[O:14])=[N:11][C:7]=3[C:6]=2[CH:32]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86693510HCID 86693510, compound

Product 1

HCID 86693511HCID 86693511, compoundYield 86%

Conditions

Temperature
50 °C

Procedure

A pressure tube containing a solution of ethyl 9-iodo-3((1-methyl-1H-indazol-3-yl)methyl)-3,4,5,6-tetrahydro-4,6-methanobenzo[3,4]cyclohepta[1,2-d]imidazole-2-carboxylate (198 mg, 0.37 mmol) in methanolic ammonia (7 mL of 7.0M ammonia in methanol) was warmed to 50° C. for 8 days. After evaporation of the reaction mixture in vacuo, the residue was suspended in methanol (0.8 mL) and the solid collected by vacuum filtration to furnish the title compound as an off-white solid (164 mg, 0.32 mmol, 86%): 1H NMR (250 MHz, CDCl3) δ1.48-1.57 (m, 2H), 2.71-2.87 (m, 2H), 3.52 (td, J=8.15, 4.42 Hz, 1H), 3.79 (td, J=7.54, 3.81 Hz, 1H), 3.99 (s, 3H), 5.44 (br. s., 3H), 6.24 (s, 2H), 6.78 (d, J=7.92 Hz, 1H), 7.03-7.11 (m, 1H), 7.31-7.41 (m, 3H), 7.53 (dt, J=8.22, 0.91 Hz, 1H), 8.71 (d, J=1.83 Hz, 1H); M+H=510.

Workup

  1. customAfter evaporation of the reaction mixture in vacuo
  2. filtrationthe solid collected by vacuum filtration

Sources & evidence

ORD record
ord-976c04d5f0d14cd388762963cf7a1548
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

Loading…