Dimethylamine → HCID 71230715, compound

HRID 589517Notes

Reaction equation

HRID 589517 reaction equation
[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[C:25]([C:27]5[CH2:32][CH2:31][C:30](=O)[CH2:29][CH:28]=5)[NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH2:34][OH:35])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:38]NC.[C:41]([BH3-])#[N:42].[Na+]>C(Cl)Cl.CO.CC(O)=O>[C:1]([C:5]1[CH:37]=[CH:36][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[C:19]4[CH:26]=[C:25]([C:27]5[CH2:32][CH2:31][CH:30]([N:42]([CH3:41])[CH3:38])[CH2:29][CH:28]=5)[NH:24][C:20]=4[N:21]=[CH:22][N:23]=3)[C:13]=2[CH2:34][OH:35])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 71231450HCID 71231450, compound

Product 1

HCID 71230715HCID 71230715, compound

Reagents, catalysts & solvents 1

HCID 21877243DCM MeOH AcOHSolvent

Procedure

To a solution of Intermediate 49 (100 mg, 0.202 mmol) in DCM/MeOH/AcOH (4 ml, 100:93:7) was added dimethylamine (91 mg, 2.02 mmol). The mixture was stirred for 15 min at r.t. before adding sodium cyanoborohydride (12.7 mg, 0.202 mmol). The mixture was stirred at r.t. overnight and then quenched with 2N HCl (3 ml). After additional stirring for 30 min water and 2N NaOH were added. The mixture was extracted with EtOAc, and the organic layer was dried, filtered, and evaporated to dryness. The resulting residue was purified using flash chromatography (silica gel, EtOAc/MeOH/NH4OH gradient) to yield Example 56.

Workup

  1. stirringThe mixture was stirred at r.t. overnight
  2. customquenched with 2N HCl (3 ml)
  3. stirringAfter additional stirring for 30 min water and 2N NaOH
  4. additionwere added
  5. extractionThe mixture was extracted with EtOAc
  6. customthe organic layer was dried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resulting residue was purified
  10. customto yield Example 56

Sources & evidence

ORD record
ord-85c7e9923e824cc79940b7d55074b95f
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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