Diisopropylethylamine → HCID 11511828, compound

HRID 1169834Notes

Reaction equation

HRID 1169834 reaction equation
[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]([CH3:21])([C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH3:8])=[O:5].CC[N:29]([CH:33]([CH3:35])C)[CH:30](C)C.N1(N[S:41](Cl)(=[O:43])=[O:42])CCC1>CN(C=O)C>[Cl:1][C:2]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:3]=1[C:4]([NH:6][C:7]([CH3:21])([C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:14][CH2:13][N:12]([S:41]([N:29]2[CH2:30][CH2:35][CH2:33]2)(=[O:43])=[O:42])[CH2:11][CH2:10]1)[CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57452079HCID 57452079, compoundHCID 68689667HCID 68689667, compound

Product 1

HCID 11511828HCID 11511828, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,4-Dichloro-N-{1-methyl-1-[4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (V-1, 45 mg, 0.12 mmol) in DMF (1 mL) was cooled in an ice bath and treated with i-Pr2NEt (0.086 mL, 0.49 mmol) followed by azetidinylsulfamoyl chloride (literature reference J. Chem. Soc. Perkin 1 1994, p1595) (29 mg, 0.19 mmol). The mixture was allowed to warm to room temperature and stirred at room temperature for 12 h. The volatile components were removed in vacuo and the residue purified by preparative TLC eluting with 3% methanol-DCM to afford 2,4-dichloro-N-{1-methyl-1-[1-(azetidinesulfonyl)-4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (V-2). 1H NMR (CDCl3, 500 MHz) δ 8.55 (d, J=3.4 Hz, 1H), 7.71 (t, J=7 Hz, 1H), 7.57 (d, J=8 Hz, 1H), 7.37 (m, 2H), 7.27 (m, 1H), 7.19 (m, 1H), 7.08 (s, 1H), 3.90 (t, J=7.5 Hz, 4H), 3.84 (d, J=6.5 Hz, 2H),), 3.46 (m, 2H), 3.30 (m, 2H), 2.31 (m, 2H), 2.22 (m, 2H), 1.94 (m, 2H); MS 483 (M+H).

Workup

  1. customThe volatile components were removed in vacuo
  2. customthe residue purified by preparative TLC
  3. washeluting with 3% methanol-DCM

Sources & evidence

ORD record
ord-3f8f32e4effa4ac780479c6a12b75d32
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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