Formaldehyde → HCID 73056044, compound

HRID 1779110Notes

Reaction equation

HRID 1779110 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][C:28]([NH2:30])=[O:29])[C:16]([C:31]([F:34])([F:33])[F:32])=[CH:15][N:14]=3)[CH:9]=[N:8]2)[CH2:3][CH2:2]1.[CH2:35]=O>CO>[CH3:35][N:1]1[CH2:2][CH2:3][CH:4]([N:7]2[CH:11]=[C:10]([NH:12][C:13]3[N:18]=[C:17]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH2:27][C:28]([NH2:30])=[O:29])[C:16]([C:31]([F:33])([F:32])[F:34])=[CH:15][N:14]=3)[CH:9]=[N:8]2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 73056043HCID 73056043, compound

Product 1

HCID 73056044HCID 73056044, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaHB(OAc)3 (147 mg, 0.693 mmol) was added cautiously to a stirred solution of 2-(2-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)acetamide (35) (82 mg, 0.17 mmol) in 37% aqueous formaldehyde solution (39 μL, 0.52 mmol) and MeOH (5.0 mL). The reaction mixture was stirred for 1 hr and then quenched with water (50 mL). The resultant precipitate was removed by filtration, washed with cyclohexane and dried under high vacuum to yield the title compound as a white solid (82 mg, 97%). LCMS-A: rt 4.751 min; m/z 488.3 [M+H]+.

Workup

  1. customquenched with water (50 mL)
  2. customThe resultant precipitate was removed by filtration
  3. washwashed with cyclohexane
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-87e5f879bc894f4c9f40e55765e3daaa
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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