Water → HCID 68089376, compound

HRID 449166Notes

Reaction equation

HRID 449166 reaction equation
[C:1]([C:3]1[CH:48]=[CH:47][C:6]([CH2:7][C@@:8]2([CH3:46])[N:12]3[C:13]([C:16]([NH:18][C:19]4([C:22]([NH:24][C:25]5([C:28]6[CH:29]=[C:30]([CH:34]=[CH:35][N:36]=6)C(O)=O)[CH2:27][CH2:26]5)=[O:23])[CH2:21][CH2:20]4)=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:37]3[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([Cl:44])[CH:38]=3)[C:9]2=[O:45])=[CH:5][CH:4]=1)#[N:2].CN([C:52]([O:56]N1N=NC2C=CC=NC1=2)=[N+:53]([CH3:55])C)C.F[P-](F)(F)(F)(F)F.[OH2:73].C[N:75]([CH:77]=[O:78])[CH3:76]>>[C:3]([O:73][C:77](=[O:78])[NH:75][CH2:76][CH2:55][NH:53][C:52]([C:34]1[CH:35]=[N:36][C:28]([C:25]2([NH:24][C:22]([C:19]3([NH:18][C:16]([C:13]4[N:12]5[C@@:8]([CH2:7][C:6]6[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:48][CH:47]=6)([CH3:46])[C:9](=[O:45])[N:10]([C:37]6[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([Cl:44])[CH:38]=6)[C:11]5=[N:15][CH:14]=4)=[O:17])[CH2:21][CH2:20]3)=[O:23])[CH2:26][CH2:27]2)=[CH:29][CH:30]=1)=[O:56])([CH3:48])([CH3:4])[CH3:1]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68089304HCID 68089304, compound

Product 1

HCID 68089376HCID 68089376, compound

Procedure

To 2-{1-[(1-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-amino]-cyclopropyl}-isonicotinic acid (30 mg, 0.044 mmol), in DMF (3 mL) was added HATU (50 mg, 0.13 mmol) diisopropylethylamine (23 μL, 0.13 mmol) and mono-Boc-protected ethylenediamine (14 mg, 0.088 mmol). The reaction was shaken at room temperature overnight. Water was added (0.1 mL) and the crude reaction was purified by HPLC to afford {2-[(6-{1-[(1-{[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-carbonyl]-amino}-cyclopropanecarbonyl)-amino]-cyclopropyl}-pyridine-3-carbonyl)-amino]-ethyl}-carbamic acid tert-butyl ester. This material was dissolved in dichloromethane (1.0 mL) and 4M HCl in dioxane (0.5 mL) was added. The reaction was shaken for 2 h at room temperature. The volatiles were removed to afford 23 mg of the title compound, m/z 726.3.

Workup

  1. customthe crude reaction
  2. customwas purified by HPLC

Sources & evidence

ORD record
ord-9d4460f77cac446ab9fc3f000f247f67
Source dataset
uspto-grants-2013_07
Patent number
US08481750B2

Reaction notes

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