Hydrochloric Acid → HCID 51002051, compound

HRID 2088430Notes

Reaction equation

HRID 2088430 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][CH:10]=[C:11]([C:13]([NH:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[N:22]2[CH2:27][CH2:26][CH2:25][C@H:24]([NH:28]C(=O)OC(C)(C)C)[CH2:23]2)=[O:14])[N:12]=1.Cl>O1CCOCC1>[NH2:28][C@H:24]1[CH2:25][CH2:26][CH2:27][N:22]([C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:15][C:13]([C:11]2[N:12]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[S:9][CH:10]=2)=[O:14])[CH2:23]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58182165(S)-tert-butyl 1-(3-(2-(2-fluorophenyl)thiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate

Product 1

HCID 51002051HCID 51002051, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (S)-tert-butyl 1-(3-(2-(2-fluorophenyl)thiazole-4-carboxamido)pyridin-4-yl)piperidin-3-ylcarbamate (100 mg, 0.2 mmol) in 1,4-Dioxane (6 mL) was added 4.0 M of Hydrogen chloride in 1,4-Dioxane (3 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC. (10.7 mg, 10.0%). 1H NMR (400 MHz, DMSO) δ 9.24 (s, 1H), 8.68 (s, 1H), 8.40 (t, J=7.1, 1H), 8.32-8.26 (m, 2H), 7.67-7.61 (m, 1H), 7.53-7.43 (m, 2H), 7.16 (d, J=5.3, 1H), 3.04 (s, 2H), 2.75 (t, J=9.5, 1H), 2.61-2.54 (m, 1H), 1.92-1.86 (m, 1H), 1.81 (d, J=4.2, 1H), 1.73 (d, J=9.9, 1H), 1.33-1.23 (m, 1H); ESIMS m/z=398.1 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a64b4fe111034c41a38427402ed0d9ee
Source dataset
uspto-grants-2013_05
Patent number
US08435976B2

Reaction notes

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