Formaldehyde → HCID 18771958, compound

HRID 460251Notes

Reaction equation

HRID 460251 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][C:10]2[N:15]=[C:14]([NH:16][C:17]([NH:19][C:20]3[N:21]=[C:22]([C:25]4[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=4)[S:23][CH:24]=3)=[O:18])[CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:35](C)=O.[Na+]>C(Cl)Cl>[CH3:35][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][O:9][C:10]2[N:15]=[C:14]([NH:16][C:17]([NH:19][C:20]3[N:21]=[C:22]([C:25]4[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=4)[S:23][CH:24]=3)=[O:18])[CH:13]=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 18771846HCID 18771846, compound

Product 1

HCID 18771958HCID 18771958, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-[2-(4-pyridinyl)-4-thiazolyl]-N′-2-[6-(4-piperidinylethoxy)pyridinyl]urea (0.17 g, 0.40 mmol, Example 167), paraformaldehyde (0.17 g), and NaBH(OAc)3 (0.21 g, 1.0 mmol) in 40 mL of CH2Cl2 was stirred at RT under N2 for 12 h. After 12 h, the solvent was removed in vacuo, and the residue was diluted with 20 mL of H2O, then extracted with CHCl3/IpOH (3:1, 3×20 mL). The combined organic portions were washed with brine, and dried over MgSO4, and the solvents were removed in vacuo to yield a residue. Purification over silica gel (gradient, 5% to 7.5% MeOH/CH2Cl2 with 0.5% of TEA) provided the title compound as an off-white solid. MS m/z: 439 (M+H). Calc'd for C22H26N6O2S: 438.18.

Workup

  1. waitAfter 12 h
  2. customthe solvent was removed in vacuo
  3. additionthe residue was diluted with 20 mL of H2O
  4. extractionextracted with CHCl3/IpOH (3:1, 3×20 mL)
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvents were removed in vacuo
  8. customto yield a residue
  9. customPurification over silica gel (gradient, 5% to 7.5% MeOH/CH2Cl2 with 0.5% of TEA)

Sources & evidence

ORD record
ord-9f57f625a0484665b9de3efed9e88743
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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