Formaldehyde → HCID 67172824, compound

HRID 872912Notes

Reaction equation

HRID 872912 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]4[CH2:28][NH:27][CH2:26][CH2:25][N:24]4[CH:29]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH2:30](N(CC)CC)C.C=O.O.C([BH3-])#N.[Na+]>CO.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:14]=[CH:13][N:12]([CH2:15][C@@H:16]([NH:18][C:19]([C:21]3[N:22]=[C:23]4[CH2:28][N:27]([CH3:30])[CH2:26][CH2:25][N:24]4[CH:29]=3)=[O:20])[CH3:17])[N:11]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 962WaterHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 67173103HCID 67173103, compound

Product 1

HCID 67172824HCID 67172824, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(S)—N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyrazine-2-carboxamide (23 mg, 0.056 mmol) was dissolved in methanol (2 ml). Triethylamine (0.078 ml, 0.561 mmol), formaldehyde, 37 w-% solution in water (0.067 ml, 0.561 mmol) and sodium cyanoborohydride (35.3 mg, 0.561 mmol) were added in the solution. The resulting mixture was stirred at RT overnight. The reaction mixture was diluted with DCM, extracted with NaHCO3 solution, combined organic phases were dried with Na2SO4, filtered and evaporated. The product was purified with LC/MS-trigger. Yield 33.6%. 1H-NMR (400 MHz; CDCl3): δ 1.26 (d, 3H), 2.55 (s, 3H), 2.90 (t, 2H), 3.70 (d, 2H), 4.08 (t, 2H), 4.32 (dd, 1H), 4.40 (dd, 1H), 4.54-4.65 (m, 1H), 6.61 (d, 1H), 7.48 (s, 1H), 7.50 (d, 1H), 7.67 (d, 1H), 7.71 (d, 1H), 7.81 (dd, 1H), 8.02 (d, 1H), 8.06 (s, 1H).

Workup

  1. extractionextracted with NaHCO3 solution
  2. dry with materialwere dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product was purified with LC/MS-trigger

Sources & evidence

ORD record
ord-db4bf8f903ed44abbe818c40855b8835
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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