Hydrochloric Acid → 3-phenoxy-N-(4-(piperidin-4-ylmethyl)thiazol-2-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine dihydrochloride

HRID 1806190Notes

Reaction equation

HRID 1806190 reaction equation
[ClH:1].O1CCOCC1.[O:8]([C:15]1[C:16]([NH:31][C:32]2[S:33][CH:34]=[C:35]([CH2:37][CH:38]3[CH2:43][CH2:42][N:41](C(OC(C)(C)C)=O)[CH2:40][CH2:39]3)[N:36]=2)=[N:17][CH:18]=[C:19]([S:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[CH:28]=[CH:29][S:30][C:23]=23)[CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl.CO>[ClH:1].[ClH:1].[O:8]([C:15]1[C:16]([NH:31][C:32]2[S:33][CH:34]=[C:35]([CH2:37][CH:38]3[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]3)[N:36]=2)=[N:17][CH:18]=[C:19]([S:21][C:22]2[CH:27]=[CH:26][N:25]=[C:24]3[CH:28]=[CH:29][S:30][C:23]=23)[CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57742604tert-butyl 4-((2-(3-phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-Ylamino)thiazol-4-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 866315353-phenoxy-N-(4-(piperidin-4-ylmethyl)thiazol-2-yl)-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-amine dihydrochlorideYield 98.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Added 4N HCl in dioxane (3.0 mL, 12.0 mmol) to a solution of tert-butyl 4-((2-(3-phenoxy-5-(thieno[3,2-b]pyridin-7-ylthio)pyridin-2-ylamino)thiazol-4-yl)methyl)piperidine-1-carboxylate (0.790 g, 1.25 mmol) in dichloromethane (4 mL) and methanol (4 mL). The reaction was stirred at ambient temperature for 3 hours. Concentrated, triturated with hexanes, filtered to afford the title compound (0.745 g, 98.5% yield) as a light yellow powder: 1H NMR (d6-DMSO) δ 9.13 (m, 1H), 8.89 (m, 1H), 8.67 (d, 1H), 8.51 (d, 1H), 8.47 (s, 1H), 7.80 (d, 1H), 7.57 (s, 1H), 7.42 (t, 2H), 7.16-7.23 (m, 4H), 6.91 (s, 1H), 3.21 (m, 2H), 2.80 (m, 2H), 2.60 (d, 2H), 1.95 (m, 1H), 1.76 (m, 2H), 1.45 (m, 2H).

Workup

  1. concentrationConcentrated
  2. customtriturated with hexanes
  3. filtrationfiltered

Sources & evidence

ORD record
ord-615f754f750040318957d162b9b75a0a
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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