Diisopropylethylamine → N-Cyclohexyl-N-cyclopropyl-1-(phenylsulfonyl)piperidine-3-carboxamide

HRID 656319Notes

Reaction equation

HRID 656319 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([OH:18])=O)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]1([NH:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:21][CH2:20]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:23]1([N:22]([CH:19]2[CH2:21][CH2:20]2)[C:16]([CH:12]2[CH2:13][CH2:14][CH2:15][N:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:8])=[O:9])[CH2:11]2)=[O:18])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27699561-(Phenylsulfonyl)piperidine-3-carboxylic acidHCID 20114456N-Cyclopropylcyclohexanamine

Product 1

HCID 11545597N-Cyclohexyl-N-cyclopropyl-1-(phenylsulfonyl)piperidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(phenylsulfonyl)piperidine-3-carboxylic acid (20 mg), N-cyclopropylcyclohexanamine (10 mg) and benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (36 mg) in DMF (200 μL) was added N,N-diisopropylethylamine (26 μL). The resulting solution was stirred at r.t. for 2 hours and directly purified with prep HPLC. LCMS m/z 391.1 (M+H)+; 803.2 (2M+Na)+.

Workup

  1. customdirectly purified with prep HPLC

Sources & evidence

ORD record
ord-f96bf4173d8446488ef56a00993cd3c7
Source dataset
uspto-grants-2011_12
Patent number
US08071624B2

Reaction notes

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