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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 3-(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl) carbamoyl)phenyl)pyrrolidine-1-carboxylate

HRID 2202032
Notes
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Reaction equation

HRID 2202032 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:43][CH2:44][CH:45]([OH:57])[CH2:46][N:47]1[CH2:56][CH2:55][C:54]2[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH2:48]1>CN(C=O)C.O>[CH2:48]1[C:49]2[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:55][CH2:56][N:47]1[CH2:46][CH:45]([OH:57])[CH2:44][NH:43][C:16]([C:15]1[CH:14]=[C:13]([CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]2)[CH:21]=[CH:20][CH:19]=1)=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 167907201-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olHCID 534066233-{1-[(Tert-butoxy)carbonyl]pyrrolidin-3-yl}benzoic acid

Product 1

HCID 90241042tert-butyl 3-(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl) carbamoyl)phenyl)pyrrolidine-1-carboxylate
Yield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
31 °C

Procedure

To a solution of 3-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)benzoic acid (200 mg, 0.69 mmol) in DMF (4 ml) was added TEA (208 mg, 2.06 mmol), HOBt (139 mg, 1.03 mmol), EDCI (197 mg, 1.03 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (170 mg, 0.82 mmol) at 33° C. The reaction mixture was stirred for 16 h at 31° C. The mixture was treated with water and extracted with EA. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification (300 mg, Yield 92%).

Workup

  1. extractionextracted with EA
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-32a968c95f584f1b80482c85da9ccd8e
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365519B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes