Water → HCID 90047129, compound

HRID 1754252Notes

Reaction equation

HRID 1754252 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[O:6][C:7]([CH2:10][C:11]3[S:12][C:13]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:17]=[CH:16][C:14]=4[N:15]=3)=[N:8][N:9]=2)[CH2:2]1.[CH:26](=O)[C:27]([CH3:30])([CH3:29])[CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl.C(O)(=O)C>[CH2:26]([N:1]1[CH2:4][CH:3]([C:5]2[O:6][C:7]([CH2:10][C:11]3[S:12][C:13]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH:17]=[CH:16][C:14]=4[N:15]=3)=[N:8][N:9]=2)[CH2:2]1)[C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 90047641HCID 90047641, compound

Product 1

HCID 90047129HCID 90047129, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Compound 42a (117 mg, 0.34 mmol), pivalaldehyde (57.8 mg, 0.67 mmol), sodium triacetoxyborohydride (27.4 mg, 0.13 mmol), and acetic acid (0.123 μl, 2.15 μmol) were stirred in dichloromethane (0.05 mL) at rt for 24 h. H2O was added, followed by CH2Cl2. The organic layer was separated, dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by preparative HPLC (HPLC method D) to give Compound 42b (60 mg, 43% yield) as a tan film. LCMS ESI 419.1 (M+MeOH+H), RT=1.80 min (Method B). 1H NMR (500 MHz, CD3OD-d4) d 8.25 (d, J=1.65 Hz, 1H), 7.97-8.05 (m, 1H), 7.81 (dd, J=1.93, 8.53 Hz, 1H), 7.64-7.73 (m, 2H), 7.42-7.53 (m, 2H), 7.30-7.41 (m, 1H), 4.64-4.92 (m, 5H), 4.34-4.53 (m, 2H), 3.22-3.29 (m, 2H), 1.06 (s, 9H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. custompurified by preparative HPLC (HPLC method D)

Sources & evidence

ORD record
ord-924aaf2c31924e51b967e733f4ade0cf
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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