HCID 59452209, compound → HCID 25131970, compound

HRID 2381156Notes

Reaction equation

HRID 2381156 reaction equation
CC1(C)[O:6][C@@H:5]([CH2:7][O:8][NH:9][C:10]([C:12]2[N:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=3[F:30])[C:15]3=[CH:16][N:17]=[CH:18][C:19]([Br:20])=[C:14]3[CH:13]=2)=[O:11])[CH2:4][O:3]1>ClCCl>[OH:6][C@H:5]([CH2:4][OH:3])[CH2:7][O:8][NH:9][C:10]([C:12]1[N:21]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([I:29])=[CH:25][C:24]=2[F:30])[C:15]2=[CH:16][N:17]=[CH:18][C:19]([Br:20])=[C:14]2[CH:13]=1)=[O:11]

Participants

3

Reactant 1

HCID 59452209HCID 59452209, compound

Product 1

HCID 25131970HCID 25131970, compoundYield 13.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-bromo-1-(2-fluoro-4-iodo-benzyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-amide (40 mg, 66 μmol) in dichloromethane (1.5 ml) was loaded onto a SCX-2 SPE cartridge. The desired compound was eluted from the cartridge with a solution of ammonia in methanol to afford a residue. The residue was further purified by flash chromatography (Si-SPE, ethyl acetate, dichloromethane:methanol 90:10 to 80:20) afforded the title compound as a pale yellow gum (5 mg, 13%). LCMS (Method A): RT=3.51 min, (M−H)−=562, 564, M+H+=564, 566. 1H NMR (CD3OD): 3.62 (2H, m), 3.89 (1H, m), 3.94 (1H, dd, J=10.2, 6.4 Hz), 4.05 (1H, dd, J=10.2, 3.7 Hz), 5.92 (2H, s), 6.63 (1H, t, J=8.0 Hz), 7.04 (1H, s), 7.40 (1H, dd, J=8.0, 1.6 Hz), 7.49 (1H, dd, J=9.7, 1.6 Hz), 8.29 (1H, s), 8.79 (1H, s).

Workup

  1. washThe desired compound was eluted from the cartridge with a solution of ammonia in methanol
  2. customto afford a residue
  3. customThe residue was further purified by flash chromatography (Si-SPE, ethyl acetate, dichloromethane:methanol 90:10 to 80:20)

Sources & evidence

ORD record
ord-8be155f93b3848fdabfd597c47f58b97
Source dataset
uspto-grants-2012_09
Patent number
US08258152B2

Reaction notes

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