Cyclopropanecarbonyl chloride → HCID 86602691, compound

HRID 851987Notes

Reaction equation

HRID 851987 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([C@@H:18]2[CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]2=[O:25])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1>C(Cl)Cl>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([S:8]([N:7]([CH2:6][C:5]2[CH:26]=[CH:27][C:2]([NH:1][C:40]([CH:37]3[CH2:39][CH2:38]3)=[O:41])=[CH:3][CH:4]=2)[C@@H:18]2[CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]2=[O:25])(=[O:10])=[O:9])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 11582244HCID 11582244, compound

Product 1

HCID 86602691HCID 86602691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-Amino-benzyl)-4-chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide (0.024 g, 0.06 mmol) was dissolved in CH2Cl2 (1 ml) and Hünig's base (0.01 ml, 0.07 mmol) and cyclopropanecarbonyl chloride (0.007 ml, 0.07 mmol) were added. After 30 min at r.t. the solvent was removed under reduced pressure and the residue dissolved in ethyl acetate and washed with 5% KHSO4/10% K2SO4, brine, dried (Na2SO4), filtered and concentrated. The crude was purified using preparative RP(C18) chromatography: lyophilisate 9 mg; MS: m/e=493.4 (MNH4+).

Workup

  1. customAfter 30 min at r.t. the solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with 5% KHSO4/10% K2SO4, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was purified

Sources & evidence

ORD record
ord-be6e8cfb78b04ade8baed32f131362e4
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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