Morpholine → HCID 59618804, compound

HRID 1691447Notes

Reaction equation

HRID 1691447 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([CH:25]=O)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:27]=[C:28]([C:31]([F:34])([F:33])[F:32])[CH:29]=[CH:30][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.[BH3-]C#N.[Na+]>CCO.C([O-])(O)=O.[Na+]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([CH2:25][N:35]4[CH2:40][CH2:39][O:38][CH2:37][CH2:36]4)[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:27]=[C:28]([C:31]([F:33])([F:34])[F:32])[CH:29]=[CH:30][C:16]=3[CH2:15]2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 86649042HCID 86649042, compound

Product 1

HCID 59618804HCID 59618804, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine-8-carbaldehyde (Step A, Example 453, 10 mg, 0.020 mmol) in EtOH (2 mL) at rt was added morpholine (10 uL, 0.12 mmol) and NaCNBH3 (100 mg). After stirring at rt overnight, the reaction was diluted with sat. NaHCO3, and product was extracted with EtOAc (3×). The combined extracts were washed with brine, dried with MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc/hexanes) to give the title compound. 1H NMR (500 MHz, (CD3)2CO): δ, 8.31 (s, 1H), 7.71 (d, 1H), 7.46 (s, 1H), 7.27 (s, 2H), 7.20 (d, 2H), 7.12 (d, 1H), 6.97 (d, 2H), 4.82 (br s, 2H), 3.66 (t, 4H), 3.51 (s, 2H), 2.46 (br, 4H), 1.24 (s, 9H). LCMS: m/e 561.1 (M+H)+.

Workup

  1. extractionwas extracted with EtOAc (3×)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9ba3d406ce9748f09e5a7f102bbc59cf
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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