Formaldehyde → HCID 57732871, compound

HRID 1806500Notes

Reaction equation

HRID 1806500 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH:26]=O)[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH3:31][CH:32]([NH2:35])[CH2:33][CH3:34].[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([BH3-])#N.[Na+].C=O>CS(C)=O.C(O)(=O)C.CO.O>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][CH:9]([C:12]2[C:20]3[C:15](=[C:16]([C:28]([NH2:30])=[O:29])[CH:17]=[C:18]([C:21]4[CH:25]=[C:24]([CH2:26][N:35]([CH3:36])[CH:32]([CH3:31])[CH2:33][CH3:34])[S:23][CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

Participants

10

Reactant 5

HCID 712FormaldehydeHCID 24874Sec-ButylamineHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 577327033-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide

Product 1

HCID 57732871HCID 57732871, compoundYield 27.9%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (45 mg, 0.1 mmol) in dimethyl sulfoxide (1 mL) was added 2-butanamine (1 mmol), 1 to 2 drops of acetic acid and sodium triacetoxyborohydride (211 mg, 1 mmol). The resulting mixture was capped and stirred for 18 h followed by an addition of sodium cyanoborohydride (62 mg, 1 mmol) in methanol (0.5 mL). This was stirred for 3 h followed by an addition of formaldehyde, 37% in water, (1.5 mL). This was purified through SCX (2 g) cartridge eluting with methanol followed by NH3 in methanol. Further purification was performed by Gilson Preparatory HPLC. XBridge C18 Column (P/N 186002978) using a gradient of 10% acetonitrile to 70% acetronile in water with 0.1% NH4OH to give 14.4 mg of the title compound (27.9%).

Workup

  1. customThe resulting mixture was capped
  2. stirringThis was stirred for 3 h
  3. customThis was purified through SCX (2 g) cartridge
  4. washeluting with methanol
  5. customFurther purification

Sources & evidence

ORD record
ord-f03135d2e29449d58ce9ad048b5ed259
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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