1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 16037911, compound

HRID 1806224Notes

Reaction equation

HRID 1806224 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].[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][NH:36][CH3:37].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][N:36]([CH2:27][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[C:20]3[C:15](=[C:16]([C:29]([NH2:31])=[O:30])[CH:17]=2)[NH:14][CH:13]=[C:12]3[CH:9]2[CH2:10][CH2:11][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH2:7][CH2:8]2)[CH:26]=[CH:25][CH:24]=1)[CH3:37]

Participants

5

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 5049666Sodium triacetoxyborohydride2×HCID 577328043-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide

Product 1

HCID 16037911HCID 16037911, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(3-formylphenyl)-1H-indole-7-carboxamide (45.0 mg, 0.101 mmol) in DCM (2 mL) was added N,N,N′-trimethyl-1,2-ethanediamine (116 ul, 0.90 mmol). The reaction solution was stirred at ambient temperature for 1 hr prior to addition of NaBH(OAc)3 (69 mg, 0.326 mmol). The resulting mixture was stirred overnight at ambient temperature, and additional NaBH(OAc)3 (128 mg, 0.606 mmol) was added. The reaction was stirred for another 2 h, 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

Workup

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

Sources & evidence

ORD record
ord-f821f20ff65c41c0ae7024a6534adf95
Source dataset
uspto-grants-2013_01
Patent number
US08354406B2

Reaction notes

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