Dimethylformamide → HCID 86762273, compound

HRID 476407Notes

Reaction equation

HRID 476407 reaction equation
[C:1](C1SC=CN=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:13]([O:15][C:16]([C:18]1[N:19]=[C:20]([NH:23][C:24]([C:26]2[N:27]=[C:28]([NH:31][C:32]([O:34]C(C)(C)C)=O)[S:29][CH:30]=2)=[O:25])[S:21][CH:22]=1)=[O:17])[CH3:14].C(O)(C(F)(F)F)=O.[NH:46]1C=C[CH:48]=[CH:47]1.[CH3:51][N:52]([CH:54]=O)[CH3:53]>>[CH2:13]([O:15][C:16]([C:18]1[N:19]=[C:20]([NH:23][C:24]([C:26]2[N:27]=[C:28]([NH:31][C:32]([C:51]3[N:52]([CH3:53])[CH:54]=[C:47]([NH:46][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH:48]=3)=[O:34])[S:29][CH:30]=2)=[O:25])[S:21][CH:22]=1)=[O:17])[CH3:14]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6422Trifluoroacetic acidHCID 8027PyrroleHCID 189624871,1-Dimethylethyl 2-thiazolecarboxylateHCID 59799091HCID 59799091, compound

Product 1

HCID 86762273HCID 86762273, compoundYield 57%

Procedure

The Boc thiazole dimer (40) (0.281 g, 0.71 mmol) was deprotected using 95% TFA as described in general procedure D. The resulting residue (40′) was dissolved in dry DMF (5 mL) and the Boc protected pyrrole acid (2) (0.170 g, 0.71 mmol) was added and reacted as described in general procedure B. This yielded a yellow foam 0.210 g (57%). LCMS (method 1) rt=3.57 min; m/z (ES−) 519 (M−1).

Workup

  1. additionwas added
  2. customreacted

Sources & evidence

ORD record
ord-6a89beff8217417ab5a8fba4f44ab898
Source dataset
uspto-grants-2014_01
Patent number
US08637664B2

Reaction notes

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