Hydrochloric Acid → 2-{4-[4-((r)-1-Pyrrolidin-2-ylmethoxy)-phenoxy]-phenyl}-thiazole hydrochloride salt

HRID 1909782Notes

Reaction equation

HRID 1909782 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[S:29][CH:30]=[CH:31][N:32]=3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.[ClH:33]>O1CCOCC1>[ClH:33].[NH:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[S:29][CH:30]=[CH:31][N:32]=3)=[CH:24][CH:23]=2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68996854(R)-2-[4-(4-Thiazol-2-yl-phenoxy)-phenoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 690005622-{4-[4-((r)-1-Pyrrolidin-2-ylmethoxy)-phenoxy]-phenyl}-thiazole hydrochloride saltYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of the product of step 3 (90 mg, 0.21 mmol) in dioxane (2 ml) was added 4M HCl in dioxane (0.5 ml, 2.1 mmol), and stirred at room temperature for 4 h. After the solvent was removed, the crude material was triturated with ether to afford the title product (60 mg, 83%); 1HNMR (400 MHz, CD3OD) δ 7.90 (d, J=8.4 Hz, 2H), 7.82 (d, J=3.2 Hz, 1H), 7.55 (d, J=3.6 Hz, 1H), 7.07 (s, 4H), 7.00 (d, J=8.8 Hz, 2H), 4.22 (dd, J=10.4, 3.2, 1H), 4.14 (m, 1H), 4.04 (m, 1H), 3.38 (m, 2H), 2.28 (m, 1H), 2.14 (m, 2H), 1.92 (m, 1H); LC/MS (ESI+) 88%; m/z: 353 (M+1, 100).

Workup

  1. customAfter the solvent was removed
  2. customthe crude material was triturated with ether

Sources & evidence

ORD record
ord-f06867fbaf2c46628ad1db7d40fd30fc
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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