Acetaldehyde → HCID 12002968, compound

HRID 2374464Notes

Reaction equation

HRID 2374464 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.[CH:26](=O)[CH3:27].C([BH3-])#N.[Na+]>CO.C(=O)(O)[O-].[Na+]>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([NH:1][CH2:26][CH3:27])[N:7]=3)(=[O:11])=[O:10])=[CH:13][CH:14]=2)=[CH:19][CH:20]=1)#[N:25]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 23725123PF-915275

Product 1

HCID 12002968HCID 12002968, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of N-(6-Aminopyridin-2-yl)4′-cyanobiphenyl-4-sulfonamide (0.08 g, 0.23 mmol) in methanol (1 mL) was added acetaldehyde (0.02 mL, 0.34 mmol)) and molecular sieves (4 Å) were added. The resultant suspension was stirred for 30 minutes before the addition of sodium cyanoborohydride (0.043 g, 0.70 mmol). After 6 h, the reaction mixture was diluted with saturated aqueous sodium bicarbonate, and the aqueous layer was extracted with dichloromethane (2×10 mL). The combined organic layers was washed with brine and dried over sodium sulfate. Purification by high performance flash chromatography (25% EtOAc in hexanes) gave the product (0.055g, 63%). 1H NMR (400 MHz, CDCl3), δ: 8.03 (d, J=8.6 Hz, 2H), 7.73 (d, J=8.6 Hz, 2H), 7.65 (d, J=8.6 Hz, 2H), 7.62 (d, J=8.6 Hz, 2H), 7.40 (t, J=8.3 Hz, 1H), 6.64 (d, J=8.1 Hz, 1H), 5.88 (d, J=8.3 Hz, 1H), 3.10-3.21 (m, 2H) 1.23 (t, J=7.2 Hz, 3H); LRMS (ESI) m/z: 379.12; Anal. Calcd for C20H18N4O2S: C, 63.47; H, 4.79; N, 14.80. Found: C, 63.11; H, 4.82; N, 14.63.

Workup

  1. additionwere added
  2. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customPurification by high performance flash chromatography (25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3cb712d18fa748bb8d94487d2bdf9179
Source dataset
uspto-grants-2008_12
Patent number
US07462634B2

Reaction notes

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