Chlorosuccinimide → HCID 59542546, compound

HRID 1809051Notes

Reaction equation

HRID 1809051 reaction equation
[Cl:1]N1C(=O)CCC1=O.[N:9]1([C:16]([C:18]2[CH:22]=[C:21]([CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[S:20][CH:19]=2)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C(O)(=O)C.O>[N:9]1([C:16]([C:18]2[CH:22]=[C:21]([CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[S:20][C:19]=2[Cl:1])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 42644588HCID 42644588, compound

Product 1

HCID 59542546HCID 59542546, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

N-Chlorosuccinimide (0.024 g, 0.18 mmol) was added to a solution of azepan-1-yl-[5-(tetrahydro-pyran-4-yl)-thiophen-3-yl]-methanone (53 mg) in acetic acid (2 mL). The reaction mixture was heated to 100° C. for 3 minutes using microwave irradiation, then diluted with water and purified by HPLC, eluting with 20%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (38 mg). LCMS m/z 328.17 [M+H]+ RT=10.59 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 6.6 (s, 1H), 4.05 (m, 2H), 3.7 (m, 2H), 3.5 (m, 2H), 3.4 (m, 2H), 2.9 (m, 1H), 1.9-1.5 (m, 12H).

Workup

  1. custommicrowave irradiation
  2. custompurified by HPLC
  3. washeluting with 20%-98% acetonitrile in water (0.1% formic acid)
  4. additionThe fractions containing the desired product
  5. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-9ab2f4c687ae47fcbca4715ef06574df
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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