Morpholine → HCID 136191274, compound

HRID 1354653Notes

Reaction equation

HRID 1354653 reaction equation
[Br:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:12](=[O:28])[NH:13][CH:14]=[CH:15][C:16]=3[NH:17][CH2:18][C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[OH:20])[NH:10][C:6]=2[CH:5]=[C:4]([CH:29]=O)[CH:3]=1.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.[BH3-]C#N.[Na+]>CO>[Br:1][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[C:12](=[O:28])[NH:13][CH:14]=[CH:15][C:16]=3[NH:17][CH2:18][C@H:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[OH:20])[NH:10][C:6]=2[CH:5]=[C:4]([CH2:29][N:31]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32]2)[CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 136191279HCID 136191279, compound

Product 1

HCID 136191274HCID 136191274, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-7-Bromo-2-{4-[2-(3-chloro-phenyl)-2-hydroxy-ethylamino]-2-oxo-1,2-dihydro-pyridin-3-yl}-3H-benzimidazole-5-carbaldehyde (130 mg, 0.27 mmol) in methanol (60 mL) was added morpholine (0.2 mL, excess). The reaction mixture was stirred 1 h at room temperature. Then NaCNBH3 (1M THF solution, 1.35 mL, 1.35 mmol) was added. The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The residue was purified by prep. HPLC to yield the title compound (68 mg, 45%). 1H NMR (400 MHz, CD3OD) δ 7.83 (1H, s), 7.69 (1H, s), 7.68 (1H, s), 7.24–7.54 (4H, m), 6.30 (1H, d, J=7.6 Hz), 4.89–5.02 (1H, m), 4.50 (2H, s), 3.66–3.71 (4H, m), 3.17–3.43 (6H, m). LCMS (M+H)+ m/z 558 (t=1.41 min.).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by prep

Sources & evidence

ORD record
ord-5a87c5fa19af4f7898a8f0495ab61f36
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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