1,2-Dichloroethane → HCID 67320372, compound

HRID 1053748Notes

Reaction equation

HRID 1053748 reaction equation
[C:1]([O:5][C:6]([N:8]([C@@H:13]1[C:22]2[C:17](=[C:18]([C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[C:30]([C:38]#[N:39])[CH:29]=4)[O:25][N:24]=3)[CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][CH2:14]1)[CH2:9][C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=[CH:47][CH:48]=[CH:49][C:44]=2[N:43]=N1.C(Cl)CCl.N1CCCC1>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:38]([C:30]1[CH:29]=[C:28]([C:26]2[O:25][N:24]=[C:23]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]4[C:17]=3[CH2:16][CH2:15][CH2:14][C@@H:13]4[N:8]([CH2:9][C:10](=[O:11])[N:43]3[CH2:44][CH2:49][CH2:48][CH2:47]3)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[N:27]=2)[CH:33]=[CH:32][C:31]=1[O:34][CH:35]([CH3:37])[CH3:36])#[N:39]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 67320510HCID 67320510, compound

Product 1

HCID 67320372HCID 67320372, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Prepared using General Procedure 12. To a stirring solution of (S)-2-((tert-butoxycarbonyl)(5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)amino)acetic acid INT-24 (30 mg, 0.06 mmol) in DMF (0.5 mL) were added N-hydroxybenzotriazole (15.21 mg, 0.11 mmol) and EDC (21.63 mg, 0.11 mmol). After 10 min, pyrrolidine (46 μL, 0.56 mmol) was added and the reaction mixture was stirred 18 h at room temperature. The crude reaction was diluted with sat NaHCO3 added extracted with EA. The combined organic layers were dried over Na2SO4 and purified by preparative HPLC to give 26.9 mg (82%) of (S)-tert-butyl (5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-1,2,3,4-tetrahydronaphthalen-1-yl)(2-oxo-2-(pyrrolidin-1-yl)ethyl)carbamate. LCMS-ESI (m/z) calculated for C33H39N5O5: 585.7; found 358.1 [M−tert-butyl (2-oxo-2-(pyrrolidin-1-yl)ethyl)carbamate]+, tR=4.18 min.

Workup

  1. customPrepared
  2. customThe crude reaction
  3. additionadded
  4. extractionextracted with EA
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f040bf7fb596494ca80e6764c4ecd55b
Source dataset
uspto-grants-2016_07
Patent number
US09394264B2

Reaction notes

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