7-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridine → (3R)-[7-(3-Chloro-2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-(3-methoxy-pyrrolidin-1-yl)-methanone

HRID 1063223Notes

Reaction equation

HRID 1063223 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.[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH2:30])[CH:28]=2)[NH:23][C:22]=1[CH3:31]>CCO>[Cl:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:2]3[CH:7]=[CH:6][N:5]=[C:4]4[CH:8]=[C:9]([C:11]([N:13]5[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14]5)=[O:12])[S:10][C:3]=34)[CH:28]=2)[NH:23][C:22]=1[CH3:31]

Participants

4

Reactant 2

HCID 207677657-chloro-2-[(R)-3-methoxypyrrolidine-1-carbonyl]thieno[3,2-b]pyridineHCID 222786213-chloro-2-methyl-1H-indol-5-amine

Product 1

HCID 23401161(3R)-[7-(3-Chloro-2-methyl-1H-indol-5-ylamino)-thieno[3,2-b]pyridin-2-yl]-(3-methoxy-pyrrolidin-1-yl)-methanoneYield 85.3%

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 (75 mg, 0.25 mmol) and 3-chloro-2-methyl-1H-indol-5-ylamine (45 mg, 0.25 mmol) in EtOH (10 mL) was heated to reflux. After 48 h the reaction mixture was concentrated onto silica gel (5 mL) and purified on silica gel by flash column chromatography CH2Cl2/MeOH/NH4OH (95/41) to afford the title compound as a yellow solid, (94 mg). MS: 441.2/443.2, 407.2 (MH+); HPLC Rf: 4.93 min.; HPLC purity: 98%.

Workup

  1. concentrationAfter 48 h the reaction mixture was concentrated onto silica gel (5 mL)
  2. custompurified on silica gel by flash column chromatography CH2Cl2/MeOH/NH4OH (95/41)

Sources & evidence

ORD record
ord-a560a1c50bdc4ce5a2b0c2e8b4255e6f
Source dataset
uspto-grants-2005_11
Patent number
US06964961B2

Reaction notes

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