Diisopropylethylamine → HCID 178511126, compound

HRID 708442Notes

Reaction equation

HRID 708442 reaction equation
[NH2:1][CH2:2][C:3]1[N:4]=[N:5][N:6]([CH2:8][C@@H:9]2[C@H:12]([NH:13][C:14](=[O:30])/[C:15](=[N:22]\[O:23][C:24]3([C:27]([OH:29])=[O:28])[CH2:26][CH2:25]3)/[C:16]3[N:17]=[C:18]([NH2:21])[S:19][CH:20]=3)[C:11](=[O:31])[N:10]2[S:32]([OH:35])(=[O:34])=[O:33])[CH:7]=1.Br[CH2:37][CH2:38][CH2:39][NH:40]C(=O)OC(C)(C)C.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:27]([OH:29])=[O:28].[NH2:40][CH2:39][CH2:38][CH2:37][NH:1][CH2:2][C:3]1[N:4]=[N:5][N:6]([CH2:8][C@@H:9]2[C@H:12]([NH:13][C:14](=[O:30])/[C:15](=[N:22]\[O:23][C:24]3([C:27]([OH:29])=[O:28])[CH2:26][CH2:25]3)/[C:16]3[N:17]=[C:18]([NH2:21])[S:19][CH:20]=3)[C:11](=[O:31])[N:10]2[S:32]([OH:35])(=[O:34])=[O:33])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 118379301HCID 118379301, compound

Product 1

HCID 178511126HCID 178511126, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared in analogous manner to example 28, using 1-(((Z)-(2-(((2R,3S)-2-((4-(aminomethyl)-1H-1,2,3-triazol-1-yl)methyl)-4-oxo-1-sulfoazetidin-3-yl)amino)-1-(2-aminothiazol-4-yl)-2-oxoethylidene)amino)oxy)cyclopropanecarboxylic acid (20 mg, 0.038 mmol), tert-butyl (3 bromopropyl)carbamate (60 mg, 0.252 mmol), DIPEA (0.1 mL, 0.572 mmol), and DMF (0.5 mL). The crude residue was purified by reverse phase prep HPLC (Xselect CSH, 19×100 mm, 5 μM, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min). LCMS: Rt=0.29 min, m/z=587.1 (M+1) Method 2m_acidic. 1H NMR (500 MHz, D2O) δ 8.31 (s, 1H), 8.14 (s, 1H), 6.93 (s, 1H), 5.32 (d, J=5.1 Hz, 1H), 4.86-4.78 (m, 2H), 4.73-4.66 (m, 1H assumed; obscured by solvent residual peak), 4.29 (s, 2H), 3.04-3.01 (m, 2H), 2.97-2.92 (m, 2H), 1.96 (p, J=7.9 Hz, 2H), 1.22-1.11 (m, 2H), 1.10-0.96 (m, 2H).

Workup

  1. customPrepared in analogous manner to example 28
  2. customThe crude residue was purified by reverse phase prep HPLC (Xselect CSH, 19×100 mm, 5 μM, C18 column; ACN-water with 0.1% formic acid modifier, 24 mL/min)

Sources & evidence

ORD record
ord-ed409ec33dcf451bb9c6aff0cd5139e5
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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