Hydrochloric Acid → HCID 136366008, compound

HRID 1821864Notes

Reaction equation

[C:1]1([C:7](=[N:17][O:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)[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.[ClH:29]>>[ClH:29].[NH2:21][CH2:20][CH2:19][O:18][N:17]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[NH:16][C:11]2=[CH:12][N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 136366060HCID 136366060, compound

Product 1

HCID 136366008HCID 136366008, compound

Procedure

Phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone O-(2-aminoethyl)oxime hydrochloride was prepared by treating tert-butyl 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (Example 60) with ethereal hydrogen chloride as an off-white solid (a mixture of isomers): mp 176-184° C. dec.; 1H NMR (500 MHz, CD3OD) δ 3.22 (2H, br s), 3.37 (2H, br s), 4.44-4.81 (2H, m), 6.68 (0.17H, s) 7.00 (0.83H, s), 7.37-7.54 (6H, m), 7.97-8.20 (1H, m), 8.96 (0.17H, br s), 9.14 (0.83H, br s); ESI MS m/z 281 [C16H16N4O+H]+; HPLC (Method A) 98.3% (AUC), tR=13.0 and 13.2 min.

Workup

additiona mixture of isomers): mp 176-184° C. dec.
customHPLC (Method A) 98.3% (AUC), tR=13.0 and 13.2 min.

Sources & evidence

ORD record: ord-d6554489e63a464aa6592413ee2f4bba
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

Loading…