Diisopropylethylamine → HCID 178452992, compound

HRID 708406Notes

Reaction equation

HRID 708406 reaction equation
[CH:1]([O:14][C:15](=[O:60])[C@@H:16]([O:41]/[N:42]=[C:43](/[C:47]1[N:48]=[C:49]([NH:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[S:50][CH:51]=1)\[C:44]([OH:46])=O)[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:40])[NH:26][CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[CH:21][CH:20]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:61]1([CH2:66][C@H:67]2[NH:70][C:69](=[O:71])[C@H:68]2[NH2:72])[CH:65]=[N:64][CH:63]=[N:62]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>CN(C=O)C.CCOC(C)=O>[N:61]1([CH2:66][C@@H:67]2[C@H:68]([NH:72][C:44](=[O:46])/[C:43](=[N:42]\[O:41][C@H:16]([C:15]([O:14][CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[O:60])[CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]([C:25](=[NH:40])[NH:26][CH:27]4[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:31][CH2:32]4)=[CH:23][CH:24]=3)/[C:47]3[N:48]=[C:49]([NH:52][C:53]([O:55][C:56]([CH3:58])([CH3:59])[CH3:57])=[O:54])[S:50][CH:51]=3)[C:69](=[O:71])[NH:70]2)[CH:65]=[N:64][CH:63]=[N:62]1

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 118390218(3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-oneHCID 178452995HCID 178452995, compound

Product 1

HCID 178452992HCID 178452992, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S,Z)-2-(((1-(benzhydryloxy)-3-(4-(N-(1-(tert-butoxycarbonyl)piperidin-4-yl)carbamimidoyl)phenoxy)-1-oxopropan-2-yl)oxy)imino)-2-(2-((tert-butoxycarbonyl)amino)thiazol-4-yl)acetic acid (Prepared according to WO2013110643, 72 mg, 0.085 mmol), (3S,4R)-4-((1H-1,2,4-triazol-1-yl)methyl)-3-aminoazetidin-2-one (15.7 mg, 0.094 mmol) and HATU (42.2 mg, 0.111 mmol) in DMF (854 μL) was added DIPEA (44.8 μL, 0.256 mmol). After stirring at for 3 h it was diluted with EtOAc, washed with water, NaHCO3 (aq satd), brine, dried over Na2SO4 and concentrated in vacuo, affording the title compound (82 mg, 87%) as an olive film. LCMS: Rt=0.97 min, m/z=992.5 (M+1) Method 2m_acidic.

Workup

  1. washwashed with water, NaHCO3 (aq satd), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cdfc7df89d04fa8b3ba597f5fc5b881
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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