Diisopropylethylamine → HCID 42634921, compound

HRID 445351Notes

Reaction equation

HRID 445351 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1(C(O)=O)[CH2:5][CH2:4]1.CC[N:13]([CH:17](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:27])C=CC=CC=1.[F:37][C:38]([F:56])([F:55])[C:39]1[CH:44]=[CH:43][C:42]([C@@H:45]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:48][CH2:47][NH:46]2)=[CH:41][CH:40]=1>O1CCOCC1>[F:10][C:2]([F:1])([F:9])[C:3]1([NH:13][C:17]([N:46]2[CH2:47][CH2:48][C:49]3[C:54](=[CH:53][CH:52]=[CH:51][CH:50]=3)[C@H:45]2[C:42]2[CH:41]=[CH:40][C:39]([C:38]([F:37])([F:55])[F:56])=[CH:44][CH:43]=2)=[O:27])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acidHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 42634921HCID 42634921, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1-(trifluoromethyl)cyclopropane carboxylic acid (0.36 g, 2.3 mmol), DIEA (0.41 mL, 2.3 mmol), and diphenylphosphoryl azide (0.51 mL, 2.3 mmol) in p-dioxane (8 mL) was stirred at RT for 1 h. (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.500 g, 1.8 mmol) was added and the mixture was heated to reflux for 16 h. The mixture was cooled, concentrated and purified by ISCO (0-40% EtOAc/hexanes) to give the title compound. MS (ESI, positive ion) m/z: 429 (M+1).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 16 h
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. custompurified by ISCO (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-33b22130b1b841c4847878a760cde656
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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