Triethylamine → HCID 59860369, compound

HRID 252119Notes

Reaction equation

HRID 252119 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10]2)=[N:7][CH:8]=1.C(N(CC)CC)C.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[C:25]([F:31])[CH:24]=1.[BH4-].[Na+]>CO.ClCCl>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:14][C@H:11]2[CH2:12][CH2:13][N:9]([C:6]3[N:7]=[CH:8][C:3]([Br:2])=[CH:4][N:5]=3)[CH2:10]2)=[C:25]([F:31])[CH:24]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 4311764Sodium borohydrideHCID 66854562HCID 66854562, compound

Product 1

HCID 59860369HCID 59860369, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Dissolve 1-(5-bromopyrimidin-2-yl)-pyrrolidin-3-ylamine hydrochloride (60 mg, 0.22 mmol) in methanol (10 mL) and dichloromethane (1 mL). Add triethylamine (100 μL, 0.72 mmol) and 4-bromo-2-fluorobenzaldehyde (87 mg, 0.43 mmol) and stir overnight at room temperature. Add sodium borohydride (25 mg, 0.66 mmol) and stir 1 h. Dilute the mixture with methanol and pour onto a column of Dowex® 50wx4-200. Wash with methanol, then elute with 10% triethylamine in methanol. Concentrate and chromatograph on silica gel, eluting with 20:80 to 1:1 ethyl acetate:hexanes to give the title compound as a residue. Dissolve the residue in methanol and add 1 N HCl in methanol (0.75 mL). Concentrate and dry in a vacuum oven at 60° C. overnight to give the title compound as its hydrochloride salt, as a white solid (80 mg, 80%). 1H NMR (400 MHz, MeOH-d4) 8.45 (s, 2H), 7.57-7.52 (m, 3H), 4.42-4.34 (m, 2H), 4.15-4.09 (m, 1H), 4.04-3.99 (m, 1H), 3.87-3.77 (m, 2H), 3.69-3.62 (m, 1H), 2.63-2.54 (m, 1H), 2.36-2.27 (m, 1H), MS (ES): m/z=429 [M+H].

Workup

  1. additionpour onto a column of Dowex® 50wx4-200
  2. washWash with methanol
  3. washelute with 10% triethylamine in methanol
  4. concentrationConcentrate
  5. washchromatograph on silica gel, eluting with 20:80 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-a6e21a8e769f45db8beb44a01a8106af
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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