Water → HCID 86691448, compound

HRID 540343Notes

Reaction equation

HRID 540343 reaction equation
[NH2:1][C@@H:2]([CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]([N:17]2[CH2:23][CH2:22][CH2:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[CH2:18]2)[CH:8]=1)[CH2:3][OH:4].C([O-])(=O)C.[K+].O.[N:34]#[C:35]Br>CO>[CH2:18]1[C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[CH2:21][CH2:22][CH2:23][N:17]1[C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C@H:2]2[CH2:3][O:4][C:35]([NH2:34])=[N:1]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 517044Potassium AcetateHCID 71255323HCID 71255323, compound

Product 1

HCID 86691448HCID 86691448, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To the stirred mixture of (2S)-2-amino-4-[2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-yl]butan-1-ol (110 mg, 0.3 mmol), potassium acetate (90 mg, 0.91 mmol), methanol (8 mL) and water (2 mL) was added a solution of cyanogen bromide (32.3 mg, 0.3 mmol) in cold methanol (2 mL) at 0° C. After the addition, the resulting mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure to give a residue which was purified by preparative HPLC to give 40 mg of product as a white solid (yield was 34.5%). MS obsd. (ESI+) [(M+H)+] 387. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.77 (d, J=7.2 Hz, 1 H), 7.56-7.43 (m, 3 H), 7.17-7.04 (m, 4 H), 5.91 (brs, 1 H), 4.84 (s, 2 H), 4.21 (t, J=8.0 Hz, 2 H), 4.13 (brs, 2 H), 3.87 (t, J=7.2 Hz, 1 H), 3.77 (t, J=7.2 Hz, 1 H), 3.01 (brs, 2 H), 2.94-2.89 (m, 1 H), 1.78 (brs, 2 H), 1.72-1.67 (m, 2 H).

Workup

  1. additionAfter the addition
  2. customThe solvent was removed under reduced pressure
  3. customto give a residue which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-4c1013ab18244d559036da248d59e0bf
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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