Acetic Acid → HCID 68089182, compound

HRID 1913242Notes

Reaction equation

HRID 1913242 reaction equation
[CH3:1][Si:2]([CH3:38])([CH3:37])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2N=C(C=O)C=1.[NH:39]1[CH2:44]CO[CH2:41][CH2:40]1.[CH3:45][C:46]([OH:48])=O.[BH3-][C:50]#[N:51].[Na+].[CH3:53]CO>>[O:48]1[CH2:46][CH2:45][N:39]([CH2:44][C:50]2[N:51]=[C:8]([N:7]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:34])[CH3:35])[CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:37])([CH3:1])[CH3:38])[N:13]3[N:14]=[CH:15][C:16]([C:17]4[CH:18]=[N:19][C:20]5[C:25]([CH:26]=4)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[C:12]3[CH:53]=2)[CH2:40][CH2:41]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 702Ethanol2×HCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 86664790HCID 86664790, compound

Product 1

HCID 68089182HCID 68089182, compound

Procedure

To 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (Int-8b, 0.15 g, 0.3 mmol) in EtOH (10 mL) was added morpholine (0.12 mL, 1.4 mmol) and AcOH (0.2 mL), and the resulting mixture was stirred at room temperature for 15 minutes. NaBH3CN (0.12 g, 2.0 mmol) in EtOH (1.5 mL total) was then added and the reaction mixture was stirred at room temperature for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. Saturated NaHCO3 solution (˜20 mL) was added and the mixture was stirred for 30 minutes. The mixture was transferred to a separatory funnel with CH2Cl2 (30 mL). H2O (10 mL) and brine (20 mL) were then added. Organics were extracted with CH2Cl2 (4×30 mL), dried (Na2SO4) and concentrated in vacuo to give crude product (0.2 g). LCMS: 2.01 mins, m/z=635.3 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours, at which time LC/MS analysis
  2. customconsumption of starting material
  3. additionSaturated NaHCO3 solution (˜20 mL) was added
  4. stirringthe mixture was stirred for 30 minutes
  5. customThe mixture was transferred to a separatory funnel with CH2Cl2 (30 mL)
  6. additionH2O (10 mL) and brine (20 mL) were then added
  7. extractionOrganics were extracted with CH2Cl2 (4×30 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa76e3246f5f474eb9c55c5b0fb7d4ef
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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