HCID 69050173, compound → (S)-(4-cyclobutyl-1,4-diazepan-1-yl)(2-(3-fluorobenzyl)pyrrolidin-2-yl)methanone

HRID 882772Notes

Reaction equation

HRID 882772 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:21]([N:23]1[CH2:29][CH2:28][CH2:27][N:26]([CH:30]2[CH2:33][CH2:32][CH2:31]2)[CH2:25][CH2:24]1)=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=O)(C)(C)C>CCO.Cl.O1CCOCC1>[CH:30]1([N:26]2[CH2:27][CH2:28][CH2:29][N:23]([C:21]([C@@:9]3([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=4)[CH2:10][CH2:11][CH2:12][NH:8]3)=[O:22])[CH2:24][CH2:25]2)[CH2:31][CH2:32][CH2:33]1

Participants

5

Reactant 1

HCID 69050173HCID 69050173, compound

Product 1

HCID 46887647(S)-(4-cyclobutyl-1,4-diazepan-1-yl)(2-(3-fluorobenzyl)pyrrolidin-2-yl)methanoneYield 54.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-2-(3-fluoro-benzyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (40.0 mg) in EtOH (5.0 mL) and 4 M HCl in dioxane (2.0 mL) was stirred for 10 h. The mixture was concentrated and the residue diluted with CH2Cl2 and treated with Et3N. The mixture was washed with water and concentrated to yield title compound (17 mg, 54%). MS (ESI): mass calcd. for C26H38FN3O3, 359.60; m/z found, 360.3 [M+H]+. 1H NMR (CDCl3): 7.23-6.84 (m, 4H), 3.87-3.40 (m, 4H), 3.15-3.0 (m, 1H), 2.97-2.71 (m, 4H), 2.68-2.40 (m, 4H), 2.10-1.98 (m, 3H), 1.93-1.54 (m, 9H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue diluted with CH2Cl2
  3. additiontreated with Et3N
  4. washThe mixture was washed with water
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b57c59b1d114c7182292ac91335a548
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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