Formaldehyde → HCID 11342253, compound

HRID 2367032Notes

Reaction equation

HRID 2367032 reaction equation
[OH:1][C:2]1([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[N:40][CH:39]=[CH:38][N:37]=3)=[CH:32][N:31]=2)[CH2:7][CH2:6][CH:5]([NH:8][C@H:9]2[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=3)[CH2:10]2)[CH2:4][CH2:3]1.C=O.[C:44](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[OH:1][C:2]1([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[N:40][CH:39]=[CH:38][N:37]=3)=[CH:32][N:31]=2)[CH2:3][CH2:4][CH:5]([N:8]([CH3:44])[C@H:9]2[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=3)[CH2:10]2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11421712HCID 11421712, compound

Product 1

HCID 11342253HCID 11342253, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[2-((3S)-3-{[4-Hydroxy-4-(5-pyrazin-2-ylpyridin-2-yl)cyclohexyl]amino}pyrrolidin-1-yl)-2-oxoethyl]-3-(trifluoromethyl)benzamide (29.0 mg, 0.051 mmol) and 37% aqueous formaldehyde (21 uL, 0.26 mmol) were dissolved in THF (1.0 mL). The mixture was evaporated to dryness. Then the residue was taken up in THF (1 mL) and sodium triacetoxyborohydride (24 mg, 0.11 mmol) was added. After being stirred at room temperature overnight, the mixture was purified by HPLC to provide the title compound (5.9 mg). MS (M+H) 583.3.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-c3acdba6fca140b69d0017c57c611f9c
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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