Formaldehyde → HCID 178480119, compound

HRID 712025Notes

Reaction equation

HRID 712025 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[N:16]([C@H:17]3[CH2:22][CH2:21][C@H:20]([CH2:23][C:24]#[N:25])[CH2:19][CH2:18]3)[C:8]3=[C:9]4[S:15][CH:14]=[CH:13][C:10]4=[N:11][CH:12]=[C:7]3[N:6]=2)[CH2:2]1.O1CCC[CH2:27]1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(#N)C>[CH3:27][N:1]1[CH2:4][CH:3]([C:5]2[N:16]([C@H:17]3[CH2:18][CH2:19][C@H:20]([CH2:23][C:24]#[N:25])[CH2:21][CH2:22]3)[C:8]3=[C:9]4[S:15][CH:14]=[CH:13][C:10]4=[N:11][CH:12]=[C:7]3[N:6]=2)[CH2:2]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 178511079HCID 178511079, compound

Product 1

HCID 178480119HCID 178480119, compoundYield 6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of [trans-4-(2-azetidin-3-yl-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl)cyclohexyl]acetonitrile (14 mg, 0.038 mmol) in methanol (0.5 mL)/tetrahydrofuran (0.5 mL)/acetonitrile (0.5 mL) was added 37% aq. formaldehyde solution (12 μL, 0.16 mmol). The resulting mixture was stirred at room temperature for 10 min before sodium triacetoxyborohydride (16 mg, 0.077 mmol) was added. The mixture was stirred at room temperature for 1 h and then diluted with MeOH and purified by prep-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min) to give the desired product (0.8 mg, 6%). LCMS calculated for C20H24N5S (M+H)+: m/z=366.2. Found: 366.1.

Workup

  1. additionwas added
  2. custompurified by prep-HPLC (XBridge C18 column
  3. washeluting with a gradient of acetonitrile/water containing 0.1% ammonium hydroxide, at flow rate of 60 mL/min)

Sources & evidence

ORD record
ord-a59639468e0943dbb5b71622ff23d18a
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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