1,4-Dioxane hydrochloride → HCID 86664007, compound

HRID 712294Notes

Reaction equation

HRID 712294 reaction equation
C(OC([NH:8][C:9]1([C:42]([OH:44])=[O:43])[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[CH:19][C:18]([C:21]3[CH:22]=[C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[C:24]4[S:28][C:27]([NH:29][C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[N:26][C:25]=4[CH:35]=3)=[CH:17][N:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:45].O1CCOCC1>O1CCOCC1>[ClH:45].[NH2:8][C:9]1([C:42]([OH:44])=[O:43])[CH2:10][CH2:11][N:12]([C:15]2[N:16]=[CH:17][C:18]([C:21]3[CH:22]=[C:23]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=4)[C:24]4[S:28][C:27]([NH:29][C:30]([NH:32][CH2:33][CH3:34])=[O:31])=[N:26][C:25]=4[CH:35]=3)=[CH:19][N:20]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86664008HCID 86664008, compound

Product 1

HCID 86664007HCID 86664007, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To an ice-cold solution of 4-((tert-butoxycarbonyl)amino)-1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)pyrimidin-2-yl)piperidine-4-carboxylic acid (0.02 g, 0.03 mmol) in 1,4-dioxane (2.0 mL) was added HCl-dioxane (4.0 M, 1.0 mL) solution and the reaction mixture was left to stir at rt for 30 min. After completion (by TLC), the solvent was evaporated to obtain a brownish solid material that was finally triturated with ether to afford Compound 128 (0.01 g) as a hydrochloride salt. 1H NMR (DMSO-d6): δ 1.11 (t, J=7.20 Hz, 3H), 1.87 (m, 2H), 2.11 (m, 2H), 3.19 (m, 2H), 3.40 (m, 2H), 3.93 (m, 2H), 4.12 (m, 2H), 6.99 (br s, 1H), 7.45 (m, 1H), 7.95 (br s, 2H), 8.25 (s, 1H), 8.49 (d, J=8.0 Hz, 1H), 8.62 (s, 2H), 8.80 (d, J=4.0 Hz, 1H), 8.97 (s, 1H) and 10.65 (br s, 1H). LCMS: 519.30 [M+H]+

Workup

  1. waitthe reaction mixture was left
  2. customAfter completion (by TLC), the solvent was evaporated
  3. customto obtain a brownish solid material that
  4. customwas finally triturated with ether

Sources & evidence

ORD record
ord-4543449f8c2c41de8cf0c3b196c011a2
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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