Cyclopropylamine → HCID 16036915, compound

HRID 1806249Notes

Reaction equation

HRID 1806249 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:29]([NH2:31])=[O:30])[CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=4)[CH:19]=3)[NH:14][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].[CH:32]1([NH2:35])[CH2:34][CH2:33]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[CH:32]1([NH:35][CH2:27][C:23]2[CH:22]=[C:21]([C:18]3[CH:19]=[C:20]4[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=3)[NH:14][CH:13]=[C:12]4[CH:9]3[CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:11][CH2:10]3)[CH:26]=[CH:25][CH:24]=2)[CH2:34][CH2:33]1

Participants

6

Reactant 3

HCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 16036915HCID 16036915, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (50 mg, 0.113 mmol) in DCM (2 mL) was added cyclopropanamine (19.3 mg, 0.339 mmol). The reaction solution was stirred at ambient temperature for 30 min prior to addition of HOAc (1 drop) and NaBH(OAc)3 (75 mg, 0.545 mmol). The resulting mixture was stirred overnight at ambient temperature after which time the solvent was removed under reduced pressure. The crude product was purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%) to give the title compound (18.2 mg, 34%).

Workup

  1. stirringThe resulting mixture was stirred overnight at ambient temperature after which time the solvent
  2. customwas removed under reduced pressure
  3. customThe crude product was purified by reverse phase HPLC (water/CH3CN, 0.1% TFA 10-90%)

Sources & evidence

ORD record
ord-66b77b6bffc74e518d467ac668b2963b
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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