Hydrochloric Acid → HCID 91566610, compound

HRID 851990Notes

Reaction equation

HRID 851990 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]([CH:21]2[CH2:27][CH2:26][CH2:25][CH2:24][NH:23][C:22]2=[O:28])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1.Cl>ClCCl>[O:28]=[C:22]1[CH:21]([N:7]([CH2:6][C:5]2[CH:29]=[CH:30][C:2]([NH:1][C:40]([CH:37]3[CH2:39][CH2:38]3)=[O:41])=[CH:3][CH:4]=2)[S:8]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=2)(=[O:10])=[O:9])[CH2:27][CH2:26][CH2:25][CH2:24][NH:23]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 69491436HCID 69491436, compound

Product 1

HCID 91566610HCID 91566610, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Rac-4-trifluoromethyl-benzenesulfonic acid (4-amino-benzyl)-(2-oxo-azepan-3-yl)-amide (75 mg, 0.17 mmol) is dissolved in dichloromethane (2 ml), then pyridine (80 mg, 1 mmol) and cyclopropanecarbonyl chloride (21 mg, 0.2 mmol) were added. After shaking the mixture at room temperature for 1 hour hydrochloric acid (5 ml, 0.1M) was added. The organic layer was separated evaporated and the residue was redissolved in 1 ml of dimethylformamide for preparative HPLC separation (RP—C18, eluent acetonitrile/water) to yield 12 mg (14% of the final product). MS: m/e=510.4 (MH+), 527.2 (M+NH4+).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. customevaporated
  4. dissolutionthe residue was redissolved in 1 ml of dimethylformamide for preparative HPLC separation (RP—C18, eluent acetonitrile/water)

Sources & evidence

ORD record
ord-ce94eb0df32c42f79c014bb9ec39e96b
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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