Borane → HCID 71255493, compound

HRID 540335Notes

Reaction equation

HRID 540335 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][N:2]1[C:12]1[CH:21]=[C:20]([CH2:22][CH2:23][C:24]([NH2:26])=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.B>O1CCCC1>[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][N:2]1[C:12]1[CH:21]=[C:20]([CH2:22][CH2:23][CH2:24][NH2:26])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 71255116HCID 71255116, compound

Product 1

HCID 71255493HCID 71255493, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To the mixture of 3-[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]propanamide (50 mg, 0.145 mmol) in tetrahydrofuran (5 mL) was added a tetrahydrofuran solution of borane (1.5 mL, 1.5 mmol) at 0° C., followed by stirring at 70° C. for 4 hours. After being quenched with methanol (5 mL) at 0° C., the resulting mixture was concentrated in vacuo to give a residue which was purified by flash column (ethyl acetate/hexane, 3:7) to afford 10 mg of product as a white solid. MS obsd. (ESI+) [(M+H)+] 332. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.79 (d, J=7.2 Hz, 1 H), 7.57-7.52 (m, 2 H), 7.47-7.43 (m, 1 H), 7.18-7.04 (m, 5 H), 5.24 (brs, 2 H), 4.85 (s, 2 H), 4.14 (brs, 2 H), 3.03 (brs, 2 H), 2.93 (t, J=7.2 Hz, 2 H), 1.89-1.82 (m, 4 H).

Workup

  1. customAfter being quenched with methanol (5 mL) at 0° C.
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. customto give a residue which
  4. customwas purified by flash column (ethyl acetate/hexane, 3:7)

Sources & evidence

ORD record
ord-aa3905ee5ae643999163265f7e6e49fd
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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