2-Amino-2-methyl-1-propanol → HCID 68089300, compound

HRID 449165Notes

Reaction equation

HRID 449165 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:31]([OH:33])=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(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:73][C:74]([CH3:78])([CH3:77])[CH2:75][OH:76]>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C@@:8]2([CH3:46])[N:12]3[C:13]([C:16]([NH:18][C:19]4([C:22](=[O:23])[NH:24][C:25]5([C:28]6[CH:29]=[C:30]([C:31](=[O:33])[NH:73][C:74]([CH3:78])([CH3:77])[CH2:75][OH:76])[CH:34]=[CH:35][N:36]=6)[CH2:27][CH2:26]5)[CH2:20][CH2:21]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:47][CH:48]=1)#[N:2]

Participants

6

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 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 68089300HCID 68089300, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 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 3 mL DMF was added HATU (25 mg, 0.66 mmol) diisopropylethylamine (0.3 mL) and 2-amino-2-methyl-propan-1-ol (5.8 mg, 0.66 mmol). The solution was allowed to stir at room temperature overnight (18 h). The reaction was diluted with water (5 mL), then extracted with a 5% methanol/dichloromethane solution (3×10 mL). The organic layers were combined, dried (MgSO4) and concentrated. The resulting oil was purified by reversed phase HPLC to afford 28 mg of the title compound, m/z 755.7.

Workup

  1. extractionextracted with a 5% methanol/dichloromethane solution (3×10 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting oil was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-71a119dcfd2d44a9850d9c93109a69ca
Source dataset
uspto-grants-2013_07
Patent number
US08481750B2

Reaction notes

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