1,4-Dioxane hydrochloride → HCID 59543058, compound

HRID 336501Notes

Reaction equation

HRID 336501 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C@@H:15]2[CH2:19][S:18][C:17]([C:20]3[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=4[NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:16]2)[CH2:9]1)(C)(C)C.O1CCOCC1.Cl>ClCCl>[NH2:7][C@H:8]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C@@H:15]2[CH2:19][S:18][C:17]([C:20]3[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][C:25]([Cl:29])=[CH:24][C:23]=4[NH:30][CH:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[N:16]2)[CH2:9]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59542949HCID 59542949, compound

Product 1

HCID 59543058HCID 59543058, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[(S)-1-(2-{(R)-2-[5-chloro-7-(tetrahydro-pyran-4-ylamino)-1H-indol-2-yl]-4,5-dihydro-thiazol-4-yl}-ethyl)-pyrrolidin-3-yl]-carbamic acid t-butyl ester (150 mg, 0.27 mmol) prepared in Example 169 was dissolved in dichloromethane (30 mL). 4N hydrochloric acid dioxane solution (0.34 mL, 1.35 mmol) was added thereto, and the mixture was stirred for 4 h at room temperature. After completion of the reaction, the solvent was removed under reduced pressure. The residue was recrystallized from DCM/ethylether to give the title compound (92 mg, Yield 75%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was recrystallized from DCM/ethylether

Sources & evidence

ORD record
ord-522b037cc4a24c68bc65cab40c3126fd
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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