1-Pyrrolidineethanamine → 3-Amino-5-chloro-4-methyl-6-[(2-pyrrolidin-1-yl-ethylcarbamoyl)-methoxy]-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamide

HRID 656661Notes

Reaction equation

HRID 656661 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:13][CH2:14][C:15]([OH:17])=O)=[C:8]([Cl:12])[C:9]=2[CH3:11])[S:4][C:3]=1[C:18](=[O:23])[NH:19][CH:20]1[CH2:22][CH2:21]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.[NH2:56][CH2:57][CH2:58][N:59]1[CH2:63][CH2:62][CH2:61][CH2:60]1>CN(C=O)C.C1COCC1>[CH:20]1([NH:19][C:18]([C:3]2[S:4][C:5]3=[N:6][C:7]([O:13][CH2:14][C:15](=[O:17])[NH:56][CH2:57][CH2:58][N:59]4[CH2:63][CH2:62][CH2:61][CH2:60]4)=[C:8]([Cl:12])[C:9]([CH3:11])=[C:10]3[C:2]=2[NH2:1])=[O:23])[CH2:21][CH2:22]1

Participants

8

Reactant 5

HCID 13441-PyrrolidineethanamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68436813(3-Amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid

Product 1

HCID 576644193-Amino-5-chloro-4-methyl-6-[(2-pyrrolidin-1-yl-ethylcarbamoyl)-methoxy]-thieno[2,3-b]pyridine-2-carboxylic acid cyclopropylamideYield 18.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-amino-5-chloro-2-cyclopropylcarbamoyl-4-methyl-thieno[2,3-b]pyridin-6-yloxy)-acetic acid (0.300 g, 0.843 mmol) in a 1:1 mixture of THF:DMF (2.0 ml each) are added 1-hydroxybenzotriazole hydrate (0.148 g, 1.096 mmol), N,N-diisopropylethylamine (0.163 g, 1.265 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.242 g, 1.265 mmol), and 1-(2-aminoethyl)pyrrolidine (0.289 g, 2.529 mmol). The resulting solution is stirred at room temperature for 16 hours. The reaction is quenched by the addition of water (25 ml). A yellow precipitate formed. The mixture is cooled to 0° C. and stirred for 10 minutes, then filtered. The collected solid is dried in the vacuum oven for 3 hours at 60° C. This affords the title compound as a yellow solid (0.069 g, 18%). Mass (m/z): 452.2 (M++1), 450.2 (M+−1).

Workup

  1. customThe reaction is quenched by the addition of water (25 ml)
  2. customA yellow precipitate formed
  3. temperatureThe mixture is cooled to 0° C.
  4. stirringstirred for 10 minutes
  5. filtrationfiltered
  6. customThe collected solid is dried in the vacuum oven for 3 hours at 60° C

Sources & evidence

ORD record
ord-a0846c97073b490e9bfe2d17ad0c76e4
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

Loading…