Chlorosuccinimide → HCID 42644592, compound

HRID 1809076Notes

Reaction equation

HRID 1809076 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]([N:24]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])[CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:31]N1C(=O)CCC1=O>C(O)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:18][C:19]([Cl:31])=[C:20]([C:22]([N:24]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])[CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 42644590HCID 42644590, compound

Product 1

HCID 42644592HCID 42644592, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-piperidine-1-carboxylic acid benzyl ester (0.037 g, 0.087 mmol) was dissolved in acetic acid. N-chlorosuccinimide (0.09 mmol) was added and the reaction heated to 100° C. for 2.5 minutes using microwave irradiation. The product was 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 (0.027 g). LCMS m/z 461.24 [M+H]+ RT=13.23 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 7.4-7.25 (m, 5H), 6.6 (m, 1H), 5.1 (s, 2H), 4.3 (m, 2H), 3.65 (m, 2H), 3.35 (t, 2H), 2.9-2.8 (m, 3H), 2.0-1.9 (m, 2H), 1.85-1.75 (m, 2H), 1.7-1.6 (m, 8H).

Workup

  1. custommicrowave irradiation
  2. customThe product was purified 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-a704fb60cf5e496c861e07a4a4b310e4
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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