Pyridine → HCID 139298662, compound

HRID 708430Notes

Reaction equation

HRID 708430 reaction equation
[C:1]([O:5][C:6](=[O:29])[C:7]([O:10]/[N:11]=[C:12](/[C:16]1[N:17]=[C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[S:19][CH:20]=1)\[C:13](O)=[O:14])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH2:30][C@H:31]1[C@@H:34]([CH2:35][N:36]2[CH:40]=[N:39][C:38]([CH3:41])=[N:37]2)[NH:33][C:32]1=[O:42].CCN=C=NCCCN(C)C.N1C=CC=CC=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[C:25]([O:24][C:22]([NH:21][C:18]1[S:19][CH:20]=[C:16](/[C:12](=[N:11]/[O:10][C:7]([CH3:9])([CH3:8])[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:29])/[C:13]([NH:30][C@@H:31]2[C:32](=[O:42])[NH:33][C@@H:34]2[CH2:35][N:36]2[CH:40]=[N:39][C:38]([CH3:41])=[N:37]2)=[O:14])[N:17]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 6

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 189632922-(((1-(tert-Butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid2×HCID 118380273HCID 118380273, compound

Product 1

HCID 139298662HCID 139298662, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (310 mg, 0.72 mmol), (3S,4R)-3-amino-4-((3-methyl-1H-1,2,4-triazol-1-yl)methyl)azetidin-2-one (130 mg, 0.72 mmol) and EDCI (150 mg, 0.79 mmol) in DMF (5 mL) at 0° C. was added pyridine (64 μL, 0.79 mmol). After stirring at rt for 24 h, more (Z)-2-(((1-(tert-butoxy)-2-methyl-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (310 mg, 0.72 mmol) and EDCI (150 mg, 0.79 mmol) were added, along with HOBt (110 mg, 0.79 mmol) and DIPEA (250 μL, 1.44 mmol). After an additional 16 h of stirring it was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 5%), affording the title compound (230 mg, 54%) as a white solid. LCMS: m/z=593.0 (M+1).

Workup

  1. stirringAfter an additional 16 h of stirring it
  2. concentrationwas concentrated in vacuo
  3. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 5%)

Sources & evidence

ORD record
ord-4fe62d86c5fd4bf9a8d6f03de9cd84f9
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…