Formaldehyde → HCID 86654600, compound

HRID 2384787Notes

Reaction equation

HRID 2384787 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[C:16]3[S:20][C:19]([N:21]4[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:27][OH:28])[CH2:22]4)=[N:18][C:17]3=[O:29])=[CH:12][CH:13]=2)[CH:8]=[N:7]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:44](C)=O.[Na+]>C(Cl)Cl>[F:39][C:2]([F:38])([F:1])[C:3]1[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=[CH:30][C:4]=1[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH:15]=[C:16]3[S:20][C:19]([N:21]4[CH2:26][CH2:25][N:24]([CH3:44])[C@@H:23]([CH2:27][OH:28])[CH2:22]4)=[N:18][C:17]3=[O:29])=[CH:12][CH:13]=2)[CH:8]=[N:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86654601HCID 86654601, compound

Product 1

HCID 86654600HCID 86654600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4 mL of CH2Cl2 was added 5-({1-[2,4-bis(trifluoromethyl)benzyl]-1H-indazol-5-yl}methylidene)-2-[3-(R)-(hydroxymethyl)-piperazin-1-yl]-1,3-thiazol-4(5H)-one (Example 139, 50 mg), followed by 50 mg of 37% HCHO. The mixture was stirred at room temperature for 20 min, then 50 mg of NaBH(OAc)3 was added. The reaction mixture was kept stirring for 1 h and partitioned between CH2Cl2 and water. The combined organic extracts were washed with brine, dried, and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc to MeOH/EtOAc (10/90) to afford the title product.

Workup

  1. stirringThe reaction mixture was kept stirring for 1 h
  2. custompartitioned between CH2Cl2 and water
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with EtOAc to MeOH/EtOAc (10/90)

Sources & evidence

ORD record
ord-8d68367e2fef43bd888bc308a7b9e0ec
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

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