Acetic Acid → HCID 57942109, compound

HRID 1898209Notes

Reaction equation

HRID 1898209 reaction equation
[C:1]([Si:5]([CH3:11])([CH3:10])[O:6][CH2:7][CH:8]=O)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[NH2:16][C:17]1[CH:22]=[C:21]([C:23]([C:25]2[C:30]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([C:42]([F:45])([F:44])[F:43])[CH:36]=3)(=[O:34])=[O:33])=[CH:29][C:28]([Cl:46])=[CH:27][N:26]=2)=[O:24])[CH:20]=[CH:19][N:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([Si:5]([CH3:10])([CH3:11])[O:6][CH2:7][CH2:8][NH:16][C:17]1[CH:22]=[C:21]([CH:23]([OH:24])[C:25]2[C:30]([NH:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([C:42]([F:45])([F:44])[F:43])[CH:36]=3)(=[O:34])=[O:33])=[CH:29][C:28]([Cl:46])=[CH:27][N:26]=2)[CH:20]=[CH:19][N:18]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57942159HCID 57942159, compound

Product 1

HCID 57942109HCID 57942109, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (tert-butyl-dimethyl-silanyloxy)-acetaldehyde (177.7 mg, 1.02 mmol), acetic acid (0.051 mL, 0.85 mmol) and N-[2-(2-amino-pyridine-4-carbonyl)-5-chloro-pyridin-3-yl]-4-methyl-3-trifluoromethyl-benzenesulfonamide (400 mg, 0.85 mmol) in DCM (3 mL) was stirred at RT for 1 hour. To the mixture was added sodium triacetoxyborohydride (360.8 mg, 1.7 mmol), stirred overnight. The mixture was extracted with ethyl acetate, washed with water, dried and concentrated. The residue was purified by flash column to afford N-[2-({2-[2-(tert-butyl-dimethyl-silanyloxy)-ethylamino]-pyridin-4-yl}-hydroxy-methyl)-5-chloro-pyridin-3-yl]-4-methyl-3-trifluoromethyl-benzenesulfonamide.

Workup

  1. stirringstirred overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-f539033f7efb4021a1225d52ed4fccce
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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