Carbodiimide → HCID 16678875, compound

HRID 551152Notes

Reaction equation

HRID 551152 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][C:9]([CH2:16][NH2:17])([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].N=C=N.[Cl:21][C:22]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:23]=1[C:24](O)=[O:25]>ClCCl>[Cl:21][C:22]1[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:27][C:23]=1[C:24]([NH:17][CH2:16][C:9]1([CH2:12][CH:13]([CH3:14])[CH3:15])[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])[CH2:11][CH2:10]1)=[O:25]

Participants

5

Reactant 3

HCID 160435CarbodiimideHCID 111183632-chloro-4-(trifluoromethyl)benzoic AcidHCID 57931192HCID 57931192, compound

Product 1

HCID 16678875HCID 16678875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a large glass container with a Teflon cap was placed 1-[1-(ethylsulfonyl)-4-isobutylpiperidin-4-yl]methanamine (5) (670 mg, 2.55 mmol). This was dissolved in dichloromethane (50 ml) and PS-carbodiimide resin (5.11 mmol) was then added along with 2-chloro-4-(trifluoromethyl)benzoic acid (688 mg, 3.06 mmol). The lid was sealed and the bottle was shaken for 0.5 hours. The resin was filtered off and washed with EtOAc (3×25 ml). The organics were concentrated in vacuo to give an off white solid. The residue was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to give 2-chloro-N-{[1-(ethylsulfonyl)-4-isobutylpiperidin-4-yl]methyl}-4-(trifluoromethyl)benzamide (7) as a white solid. Calculated HRMS 469.1534 Found 469.15333. 1H NMR (300 MHz D6DMSO): δ 8.85 (s, 1 H), 7.95 (s, 1 H), 7.79 (d, J=7.8 Hz, 1 H), 7.60 (d, J=8.1 Hz, 1 H), 3.34 (s, 2 H), 3.21 (s, 4 H), 3.05 (q, J=7.2 Hz, 2 H), 1.75 (m, 1 H), 1.51 (m, 4 H), 1.29 (d, J=4.8 Hz, 2 H), 1.21 (t, J=7.5 Hz, 3 H), 0.94 (s, 3 H), 0.91 (s, 3H).

Workup

  1. customThe lid was sealed
  2. filtrationThe resin was filtered off
  3. washwashed with EtOAc (3×25 ml)
  4. concentrationThe organics were concentrated in vacuo
  5. customto give an off white solid
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with EtOAc/Hexanes

Sources & evidence

ORD record
ord-614bd6e4917c490cb48e52ecd77709c7
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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