Diisopropylcarbodiimide → (S)-tert-butyl 1-((4-(5-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate

HRID 2196507Notes

Reaction equation

HRID 2196507 reaction equation
[CH3:1][O:2][C:3]1[CH:42]=[CH:41][CH:40]=[CH:39][C:4]=1[C:5]([NH:7][NH:8][C:9]([C:11]1[N:15]([C:16]2[CH:17]=[C:18]([CH2:21][NH:22][C:23](=[O:34])[C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH3:25])[S:19][CH:20]=2)[N:14]=[C:13]([C:35]([F:38])([F:37])[F:36])[CH:12]=1)=O)=[O:6].CC(C)N=C=NC(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:42]=[CH:41][CH:40]=[CH:39][C:4]=1[C:5]1[O:6][C:9]([C:11]2[N:15]([C:16]3[CH:17]=[C:18]([CH2:21][NH:22][C:23](=[O:34])[C@@H:24]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH3:25])[S:19][CH:20]=3)[N:14]=[C:13]([C:35]([F:36])([F:37])[F:38])[CH:12]=2)=[N:8][N:7]=1

Participants

4

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 69299464(S)-tert-butyl 1-((4-(5-(2-(2-methoxybenzoyl)hydrazinecarbonyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 69300925(S)-tert-butyl 1-((4-(5-(5-(2-methoxyphenyl)-1,3,4-oxadiazol-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophen-2-yl)methylamino)-1-oxopropan-2-ylcarbamateYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound 16 (73 mg, 0.120 mmol) in DMF (1.0 mL) and DIC (0.1 mL, 0.642 mmol) was heated to 100 degrees for 13 hours. The reaction was concentrated down to a brown gum and then applied onto a 12M Biotage column and eluted with 0-5% methanol and dichloromethane to give 72 mg of a semi-purified compound. This material was further purified by preparative HPLC (C18 Aquasil 20×250 mm; 40-85% methanol in water in 45 minutes at 10 mL/min) to give compound 17 (20.3 mg, 29%) as a white crust. LRMS (ESI): calc. 592.2; found 493.2 (MH-Boc)+, 593.3 (MH)+.

Workup

  1. concentrationThe reaction was concentrated down to a brown gum
  2. washeluted with 0-5% methanol and dichloromethane

Sources & evidence

ORD record
ord-ebcf3b3c14804043867b0e37dbdcf052
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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