1,4-Dioxane hydrochloride → HCID 59543058, compound

HRID 1515297Notes

Reaction equation

HRID 1515297 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-08be26028faa493ca7622e6ce10d51f8
Source dataset
uspto-grants-2012_07
Patent number
US08222414B2

Reaction notes

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