Trifluoroacetic acid → HCID 9936046, compound

HRID 1795177Notes

Reaction equation

HRID 1795177 reaction equation
[NH2:1][C@H:2]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:3]([N:5]1[CH2:10][CH2:9][C:8]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)([CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40].FC(F)(F)C(O)=O>O1CCCC1>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][C@@H:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])[C:3]([N:5]2[CH2:10][CH2:9][C:8]([CH:17]3[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]3)([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[CH2:7][CH2:6]2)=[O:4])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 9867330HCID 9867330, compound

Product 1

HCID 9936046HCID 9936046, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(R)-amino-3-(4-chlorophenyl)-1-(4-cyclohexyl-4-[1,2,4]triazol-1-ylmethyl-piperidin-1-yl)-propan-1-one, 20, (400 mg, 0.93 mmol) in tetrahydrofuran (10 mL) at 0° C. is added triethylamine (0.78 mL, 5.58 mmol) and methanesulfonyl chloride (0.09 mL, 1.11 mmol). The resulting suspension is allowed to stir at room temperature overnight and the solvent removed under reduced pressure. The crude product is purified by preparative HPLC to afford 314.5 mg (54% yield) of the desired compound as the trifluoroacetic acid salt. 1H NMR (300 MHz, CD3OD) δ 0.80–1.92 (m, 15H), 2.78–3.08 (m, 5H), 3.30–3.90 (m, 4H), 4.25–4.40 (m, 2H), 4.65–4.75 (m, 1H), 7.25–7.40 (m, 4H), 8.00–8.08 (m, 1H), 8.52 (s, 1H).

Workup

  1. customthe solvent removed under reduced pressure
  2. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-dc7fa8005a6a4e9d8fabd2fd7a193dcc
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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