Trifluoroacetic acid methylene chloride → Phenyl (1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-pyrrolidin-3-yloxime dihydrochloride

HRID 1821881Notes

Reaction equation

HRID 1821881 reaction equation
[C:1]1([C:7](=[N:17][O:18][CH:19]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]2)[C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:39]>>[ClH:39].[ClH:39].[NH:21]1[CH2:22][CH2:23][CH:19]([O:18][N:17]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)[CH2:20]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 136386506tert-butyl 3-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]pyrrolidine-1-carboxylate

Product 1

HCID 136386507Phenyl (1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-pyrrolidin-3-yloxime dihydrochlorideYield 33%

Procedure

Phenyl (1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-pyrrolidin-3-yloxime dihydrochloride (12.3 mg, 33%) was prepared as an off-white amorphous solid from tert-butyl 3-[[[phenyl (1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]pyrrolidine-1-carboxylate (Example 90) following the procedure described for Example 77, except 1:1 trifluoroacetic acid/CH2Cl2 was used: 1H NMR (500 MHz, CD3OD) major isomer δ 0.94-0.92 (1H, m), 2.33-2.35 (1H, m), 3.26-3.27 (1H, m), 3.33-3.34 (1H, m), 3.45-3.46 (1H, m), 3.58-3.60 (1H, m), 3.70-3.72 (1H, m), 5.23-5.24 (1H, m), 6.78 (1H, s), 7.53-7.57 (5H, m), 8.08 (1H, d, J=6.4 Hz), 8.22 (1H, d, J=6.5 Hz), 9.01 (1H, s); ESI MS m/z 307 [C18H18N4O+H]+; HPLC (Method A) 96.6% (AUC), tR=12.6 min.

Sources & evidence

ORD record
ord-283e559be2294517bc41275120520abf
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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