2,3-dimethyl-1H-indol-5-amine → HCID 23401160, compound

HRID 1063221Notes

Reaction equation

HRID 1063221 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14]3)=[O:12])[S:10][C:3]=12.[CH3:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[CH3:30])=[CH:27][C:26]([NH2:31])=[CH:25][CH:24]=2>CCO>[CH3:20][C:21]1[NH:22][C:23]2[C:28]([C:29]=1[CH3:30])=[CH:27][C:26]([NH:31][C:2]1[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]([N:13]4[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14]4)=[O:12])[S:10][C:3]=13)=[CH:25][CH:24]=2

Participants

4

Reactant 2

HCID 2586882,3-dimethyl-1H-indol-5-amineHCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

Product 1

HCID 23401160HCID 23401160, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (3R)-(7-chloro-thieno[3,2-b]pyridin-2-yl)-(3-methoxy-pyrrolidin-1-yl)-methanone (139 mg, 0.47 mmol) and 2,3-dimethyl-1H-indol-5-ylamine (75 mg, 0.47 mmol) in EtOH (10 mL) was heated to reflux. After 12 h the reaction mixture was concentrated onto silica gel (5 mL) and purified on silica gel by flash column chromatography CH2Cl2/MeOH/NH4OH (98.5/1/0.5) to afford the title compound as a yellow solid, (190 mg). MS: 421.3 (MH+); HPLC Rf: 4.708 min.; HPLC purity: 99%.

Workup

  1. concentrationAfter 12 h the reaction mixture was concentrated onto silica gel (5 mL)
  2. custompurified on silica gel by flash column chromatography CH2Cl2/MeOH/NH4OH (98.5/1/0.5)

Sources & evidence

ORD record
ord-8ad1109dc94644109ad7147625bd6a2f
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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