Pyrrolidine → 5-[5-(1-pyrrolidinylmethyl)-2-thienyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

HRID 2267532Notes

Reaction equation

HRID 2267532 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=2)[NH:13][CH:12]=[C:11]3[CH:20]2[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)(=[O:28])=[O:27])[CH2:22][CH2:21]2)=[CH:5][CH:4]=1)=O.[NH:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[N:37]1([CH2:1][C:3]2[S:7][C:6]([C:8]3[CH:9]=[C:10]4[C:14](=[C:15]([C:17]([NH2:19])=[O:18])[CH:16]=3)[NH:13][CH:12]=[C:11]4[CH:20]3[CH2:25][CH2:24][N:23]([S:26]([CH2:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)(=[O:28])=[O:27])[CH2:22][CH2:21]3)=[CH:5][CH:4]=2)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 590033315-(5-formyl-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide

Product 1

HCID 115052105-[5-(1-pyrrolidinylmethyl)-2-thienyl]-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(5-formyl-2-thienyl)-3-(1-{[3-(1-pyrrolidinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (8.3 mg, 0.016 mmol) in methylene chloride (5 mL) was added pyrrolidine (0.001 mL, 0.016 mmol). The reaction mixture was stirred at room temperature for 1 hour before NaBH(OAc)3 (10.2 mg, 0.048 mmol) was added. The reaction mixture was stirred at room temperature overnight and evaporated all the solvent. The residue was purified by using a Gilson semi-preparative HPLC system, eluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid) pumped at 25 mL/min to give the title compound (7 mg, 92%).

Workup

  1. additionwas added
  2. customevaporated all the solvent
  3. customThe residue was purified
  4. washeluting with 10% B to 80% B, where A=H2O (0.1% trifluoroacetic acid) and B=CH3CN (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6893a11183f04bc1aba532bbb2b4377e
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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