Formaldehyde → HCID 136932645, compound

HRID 1507508Notes

Reaction equation

HRID 1507508 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:12][C:11]=1[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1.C=O.[C:39](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:15](=[O:16])[NH:14][C:13]([CH:17]2[CH2:18][CH2:19][N:20]([CH3:39])[CH2:21][CH2:22]2)=[N:12][C:11]=1[NH:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136504489HCID 136504489, compound

Product 1

HCID 136932645HCID 136932645, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a solution of tert-butyl (3R)-3-[[5-(1,3-benzothiazol-2-yl)-6-oxo-2-(piperidin-4-yl)-1,6-dihydropyrimidin-4-yl]amino]piperidine-1-carboxylate (100 mg, 0.20 mmol, 1.00 equiv) and formaldehyde (30% in water, 22 mg, 0.73 mmol, 3.74 equiv) in dichloromethane (5 ml) was added sodium triacetoxyborohydride (62.3 mg, 0.29 mmol, 1.50 equiv). The resulting solution was stirred for 2 h at room temperature, quenched with water (5 mL), and extracted with ethyl acetate (2×5 mL). The combined organic phases were washed with brine (10 mL) and dried over anhydrous sodium sulfate. After filtration and concentration under vacuum, 100 mg of the title compound was obtained as a solid, which was used directly for next step without further purification. MS m/z [M+H]+ (ESI): 525.

Workup

  1. customquenched with water (5 mL)
  2. extractionextracted with ethyl acetate (2×5 mL)
  3. washThe combined organic phases were washed with brine (10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration under vacuum

Sources & evidence

ORD record
ord-423b483e3ee54e3d81be916eff74b9fe
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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