Diisopropylethylamine → 1-[2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]pyrrolidine-3-carboxylic acid

HRID 540241Notes

Reaction equation

HRID 540241 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC(F)(F)F)[CH:10]=2)[N:5]=[C:4]([N:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[S:20](=[O:29])(=[O:28])[CH2:19][CH2:18]2)[CH:3]=1.C[O:31][C:32]([CH:34]1[CH2:38][CH2:37][NH:36][CH2:35]1)=[O:33].[CH:39](N(CC)C(C)C)(C)C>>[O:29]=[S:20]1(=[O:28])[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[CH2:23][N:17]([C:4]2[CH:3]=[C:2]([N:36]3[CH2:37][CH2:38][CH:34]([C:32]([OH:33])=[O:31])[CH2:35]3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:39])[CH:10]=3)[N:5]=2)[CH2:18][CH2:19]1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 4114360Methyl Pyrrolidine-3-carboxylateHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

Product 1

HCID 712550861-[2-(1,1-Dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]pyrrolidine-3-carboxylic acidYield 19.8%

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (500 mg, 1.34 mmol, prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1) and methylpyrrolidine-3-carboxylate (173 mg, 1.34 mmol) and N,N-diisopropylethylamine (346 mg, 2.68 mmol) was heated with stirring in a sealed 10 mL of microwave process vial for 1.5 hours at 140° C. under microwave irradiation. The resulting mixture was purified by preparative HPLC to afford 120 mg of the pure product (yield was 19.8%).

Workup

  1. temperaturewas heated
  2. customThe resulting mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-c08ccb3dd0114882be0cab57e6f31f8f
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

Loading…