Triethylamine → HCID 59860341, compound

HRID 252130Notes

Reaction equation

HRID 252130 reaction equation
Cl.[Br:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10]2)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:22][C:23]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:24]=1[CH:25]=O.[BH4-].[Na+]>CO.C(OCC)(=O)C>[Br:2][C:3]1[N:8]=[C:7]([N:9]2[CH2:13][CH2:12][C@H:11]([NH:14][CH2:25][C:24]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:23]=3[Cl:22])[CH2:10]2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 134042,4-DichlorobenzaldehydeHCID 4311764Sodium borohydrideHCID 71643944HCID 71643944, compound

Product 1

HCID 59860341HCID 59860341, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (3S)-1-(6-bromopyridin-2-yl)-pyrrolidin-3-ylamine hydrochloride (131 mg, 0.47 mmol) in methanol. Add triethylamine (200 μL, 1.44 mmol) and 2,4-dichlorobenzaldehyde (116 mg, 0.66 mmol). Stir at room temperature overnight. Add sodium borohydride (100 mg, 2.63 mmol) and stir 2 hours. Pour onto a column of Dowex® 50wx4-200 and wash with methanol. Elute with 10:90 triethylamine:methanol, concentrate to give a residue. Chromatograph the residue on silica gel eluting with 100:0 to 40:60 ethyl acetate:hexanes to give the title compound. Combine the title compound and ethyl acetate and add 1 N hydrochloric acid in methanol (1.5 mL). Concentrate to dryness to give the hydrochloride salt of the title compound (174 mg, 85%). 1H NMR (400 MHz, MeOH-d4) δ 7.67 (d, 1H, J=2.0 Hz), 7.64 (d, 1H, J=8.0 Hz), 7.49 (dd, 1H, J=8.0, 2.0 Hz), 7.40 (t, H, J=8.0 Hz), 6.79 (d, 1H, J=8.0 Hz), 6.49 (d, 1H, J=8.0 Hz), 4.46 (s, 2H), 4.17-4.11 (m, 1H), 3.95-3.91 (m, 1H), 3.79-3.75 (m, 1H), 3.73-3.66 (m, 1H), 3.54-3.48 (m, 1H), 2.65-2.56 (m, 1H), 2.38-2.29 (m, 1H); MS (ES): m/z=400 [M+H].

Workup

  1. additionPour onto a column of Dowex® 50wx4-200
  2. washwash with methanol
  3. washElute with 10:90 triethylamine
  4. concentrationmethanol, concentrate
  5. customto give a residue

Sources & evidence

ORD record
ord-bf80d76e2951443a88dfbe3dc6eeaeab
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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