Acetone → HCID 21071652, compound

HRID 1371929Notes

Reaction equation

HRID 1371929 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][NH:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:30][C:31]([CH3:33])=O.C([BH3-])#N.[Na+].CO>CO.C(O)(=O)C.ClCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:11][CH2:12][N:13]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:25])([F:26])[F:27])[CH:16]=3)[CH:31]([CH3:33])[CH3:30])=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 21071650HCID 21071650, compound

Product 1

HCID 21071652HCID 21071652, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10129899Acetic acid methanolSolvent

Conditions

Temperature
50 °C

Procedure

Combine N-(2-(6-Chloro-1H-indol-3-yl)ethyl)-3-(2,2,3,3,3-pentafluoropropoxy)benzylamine (254 mg, 0.59 mmol) in 20 mL of 95:5 methanol-acetic acid, treat with acetone (441 μL, 5.9 mmol) followed by sodium cyanoborohydride in portions (148 mg, 2.3 mmol). Stir the reaction mixture at 50° C. overnight; then at room temperature for an additional 2 days. Remove the solvent in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 4% methanol in dichloromethane to give the title compound as a colorless oil. Dissolve the oil (237 mg, 0.49 mmol) in methanol (15 mL) and treat with a solution of ammonium chloride (27 mg, 0.49 mmol) in methanol (5 mL). Sonicate the mixture for 10 minutes before concentrating it to a tacky white solid. Dissolve the tacky solid in 10 mL of 1:1 acetonitrile-water and lyophilize to give 241 mg (96%) of the title compound as the hydrochloride: mp: 77.0–80.2° C.; 1H NMR (400 MHz, methanol-d4): 7.31 (br t, 1H, J=7.8 Hz), 7.26–7.21 (m, 1H), 7.16 (br d, 1H, J=8.4 Hz), 7.15–7.07 (m, 2H), 7.05–6.95 (m, 2H), 6.83 (dd, 1H, J=8.0, 2.0 Hz), 4.52 (t, 2H, J=12.8 Hz), 4.12 (br s, 2H), 3.53 (br s, 1H), 3.11 (br s, 2H), 2.89 (br s, 2H), 1.27 (br s, 6H); MS (APCI): m/e 475.1 (M+1).

Workup

  1. waitthen at room temperature for an additional 2 days
  2. customRemove the solvent in vacuo
  3. customto give a residue

Sources & evidence

ORD record
ord-43c1e3ad8777498fb61b285d211eb91e
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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