Borohydride → HCID 10299314, compound

HRID 1986962Notes

Reaction equation

HRID 1986962 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[CH:5][C:6]2[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]4[CH2:20][C@H:19]4[CH:21]=O)[CH2:13][CH2:12]3)=[CH:9][S:8][C:7]=2[CH:23]=1.[NH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.[BH4-]>C(Cl)Cl>[N:30]1([CH2:29][CH2:28][CH2:27][NH:26][CH2:21][C@@H:19]2[CH2:20][C@H:18]2[CH2:17][N:14]2[CH2:15][CH2:16][N:11]([C:10]3[C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:25])([F:24])[F:1])=[CH:23][C:7]=4[S:8][CH:9]=3)[CH2:12][CH2:13]2)[CH:34]=[CH:33][N:32]=[CH:31]1

Participants

5

Reactant 3

HCID 28123BorohydrideHCID 787361H-Imidazole-1-propanamineHCID 86591120HCID 86591120, compound

Product 1

HCID 10299314HCID 10299314, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (1R,2R)-2-[4-(6-Trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropanecarbaldehyde (36.8 mg, 0.1 mmol) and 1-(3-aminopropyl)imidazole (0.0235 ml, 2.1 mmol) in anhydrous methylene chloride (3 ml) is added to a solution of polymer supported borohydride (0.863 g, 3 mmol) soaked in anhydrous methylene chloride (4 ml). This mixture was shook on an orbital shaker at room temperature overnight. The reaction was then quenched with water (2 ml) and products extracted with ethyl acetate (10 ml), then washed with brine, dried with sodium sulfate, and concentrated in vacuo. Silica gel chromatography eluted with methylene chloride/methanol (95:5) yielded the pure title compound, (3-Imidazol-1-yl-propyl)-{(1R,2R)-2-[4-(6-trifluoromethyl-benzo[b]thiophen-3-yl)-piperazin-1-ylmethyl]-cyclopropylmethyl}-amine as verified by NMR and LC/MS, yielding 36.2 mg, 76%.

Workup

  1. customThe reaction was then quenched with water (2 ml) and products
  2. extractionextracted with ethyl acetate (10 ml)
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography eluted with methylene chloride/methanol (95:5)

Sources & evidence

ORD record
ord-5369a35d089e4a3e89af551359a821f7
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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