Hydrochloric Acid → HCID 67304670, compound

HRID 1888005Notes

Reaction equation

HRID 1888005 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[N:22]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([NH:32]C(=O)OC(C)(C)C)([CH3:31])[CH3:30])=[CH:25][CH:24]=3)[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:40].C(OC(C)C)(C)C>ClCCl.C(OCC)(=O)C>[ClH:40].[NH2:32][C:29]([C:26]1[CH:27]=[CH:28][C:23]([N:22]2[C:11]3=[N:12][C:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:14][CH:15]=[C:10]3[N:9]=[C:8]2[C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:24][CH:25]=1)([CH3:30])[CH3:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 86761992HCID 86761992, compound

Product 1

HCID 67304670HCID 67304670, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (1-{4-[2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl]phenyl}-1-methylethyl)carbamate (27 mg) in dichloromethane (1 mL) was added a solution of hydrogen chloride in ethyl acetate (80 ul). The reaction was allowed to stir at room temperature for 1 h. Upon completion of the reaction, diisopropylether was added to the suspension and the solid was filtered to give the product (19 mg, 71%). 400 M Hz 1H-NMR (DMSO-d6) δ: 8.90-8.70 (m, 3H), 8.37 (d, J=8.3 Hz, 2H), 8.15 (dd, J=6.0 Hz and 1.8 Hz, 1H), 8.08-8.03 (m, 3H), 7.86 (dd, J=7.3 Hz and 1.4 Hz, 1H), 7.79 (d, J=8.7 Hz, 2H), 7.67 (d, J=8.7 Hz, 2H), 7.52-7.47 (m, 2H), 7.46-7.41 (m, 1H), 6.89 (dd, J=7.3 Hz and 6.4 Hz, 1H), 1.70 (s, 6H); LCMS: 421 [M+H].

Workup

  1. additionwas added to the suspension
  2. filtrationthe solid was filtered

Sources & evidence

ORD record
ord-d484c3ed85e342379c66e3d9f78052ba
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

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