Diisopropylethylamine → HCID 140294404, compound

HRID 708502Notes

Reaction equation

HRID 708502 reaction equation
[NH2:1][C@@H:2]1[C:5](=[O:6])[NH:4][C@@H:3]1[CH2:7][N:8]1[N:12]=[C:11]([CH2:13][N:14]([C:22]([N:31]2[CH2:34][CH:33]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]2)=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:10]=[N:9]1.[CH:44]([O:57][C:58]([C:60]1([O:63]/[N:64]=[C:65](/[C:69]2[N:70]=[C:71]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[S:72][CH:73]=2)\[C:66](O)=[O:67])[CH2:62][CH2:61]1)=[O:59])([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C=O)C>[C:17]([O:16][C:15]([N:14]([CH2:13][C:11]1[CH:10]=[N:9][N:8]([CH2:7][C@@H:3]2[C@H:2]([NH:1][C:66](=[O:67])/[C:65](=[N:64]\[O:63][C:60]3([C:58]([O:57][CH:44]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)=[O:59])[CH2:62][CH2:61]3)/[C:69]3[N:70]=[C:71]([NH:74][C:75]([O:77][C:78]([CH3:81])([CH3:80])[CH3:79])=[O:76])[S:72][CH:73]=3)[C:5](=[O:6])[NH:4]2)[N:12]=1)[C:22]([N:31]1[CH2:34][CH:33]([CH2:35][NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]1)=[N:23][C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])=[O:21])([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118379536HCID 118379536, compoundHCID 118380020(Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid

Product 1

HCID 140294404HCID 140294404, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared in analogous manner to example 126 step 3, using tert-butyl ((2-(((2R,3S)-3-amino-4-oxoazetidin-2-yl)methyl)-2H-1,2,3-triazol-4-yl)methyl)((3-(((tert-butoxycarbonyl)amino)methyl)azetidin-1-yl)((tert-butoxycarbonyl)imino)methyl)carbamate (460 mg, 0.76 mmol), (Z)-2-((1-((benzhydryloxy)carbonyl)cyclopropoxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (407 mg, 0.76 mmol), DMF (8 mL), DCM (8 mL), HATU (345 mg, 0.91 mmol) and DIPEA (0.33 μL, 1.89 mmol). The crude residue was purified via silica gel chromatography (EtOAc-heptane, 0-100%) to afford the title compound (0.65 g, 76%). LCMS: Rt=1.15 min, m/z=1127.9 (M+1) Method 2m_acidic.

Workup

  1. customPrepared in analogous manner to example 126 step 3
  2. customThe crude residue was purified via silica gel chromatography (EtOAc-heptane, 0-100%)

Sources & evidence

ORD record
ord-8d1477428b5347d49c8e930fdb55b0e4
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…