Isopropyl iodide → HCID 86608841, compound

HRID 1162717Notes

Reaction equation

HRID 1162717 reaction equation
Cl.Cl.[CH3:3][O:4][C@H:5]1[CH2:9][N:8]([CH2:10][C:11](=[O:22])[NH:12][C:13]2[S:14][C:15]3[CH2:16][CH2:17][CH2:18][NH:19][C:20]=3[N:21]=2)[CH2:7][C@@H:6]1[NH:23][C:24]([C:26]1[S:27][C:28]([Cl:31])=[CH:29][CH:30]=1)=[O:25].I[CH:33]([CH3:35])[CH3:34]>C1COCC1>[CH:33]([CH:18]1[CH2:17][CH2:16][C:15]2[S:14][C:13]([NH:12][C:11]([CH2:10][N:8]3[CH2:9][C@H:5]([O:4][CH3:3])[C@@H:6]([NH:23][C:24]([C:26]4[S:27][C:28]([Cl:31])=[CH:29][CH:30]=4)=[O:25])[CH2:7]3)=[O:22])=[N:21][C:20]=2[NH:19]1)([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 6362Isopropyl iodide2×HCID 86608842HCID 86608842, compound

Product 1

HCID 86608841HCID 86608841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

94.3 A suspension of 60 mg 5-chloro-thiophene-2-carboxylic acid {(3S,4S)-4-methoxy-1-[(4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylcarbamoyl)-methyl]-pyrrolidin-3-yl}-amide dihydrochloride in 3 ml THF was treated with 0.03 ml TEA and 0.01 ml 2-iodopropane. After stirring at r.t. overnight, the reaction mixture was again treated with 0.03 ml TEA and 0.03 ml 2-iodopropane and heated to 70° C. overnight. Then, it was concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 51 mg 5-chloro-thiophene-2-carboxylic acid {(3S,4S)-1-[(5-isopropyl-4,5,6,7-tetrahydro-thiazolo[5,4]pyridin-2-ylcarbamoyl)-methyl]-4-methoxy-pyrrolidin-3-yl}-amide as yellow solid. MS 498.4 ([M+H]+)

Workup

  1. temperatureheated to 70° C. overnight
  2. concentrationThen, it was concentrated
  3. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-d04e33c9f7ed451a83efcb0044b8d59a
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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