Dimethylformamide → HCID 58312838, compound

HRID 1043512Notes

Reaction equation

HRID 1043512 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[C:24](/[CH:26]=[C:27]3/[C:28](=[O:33])[NH:29][C:30](=[O:32])[S:31]/3)[CH:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)[CH2:10][C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.CCN(C(C)C)C(C)C.[F:48][C:49]([F:60])([F:59])[O:50][C:51]1[CH:52]=[C:53]([CH2:57][NH2:58])[CH:54]=[CH:55][CH:56]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[O:32]=[C:30]1[NH:29][C:28](=[O:33])/[C:27](=[CH:26]/[C:24]2[CH:23]=[CH:22][N:21]=[C:20]([N:17]3[CH2:18][CH2:19][CH:14]([CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:10][C:11](=[O:12])[NH:58][CH2:57][C:53]4[CH:54]=[CH:55][CH:56]=[C:51]([O:50][C:49]([F:48])([F:59])[F:60])[CH:52]=4)[CH2:15][CH2:16]3)[N:25]=2)/[S:31]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 1452643-(Trifluoromethoxy)benzylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58312707HCID 58312707, compound

Product 1

HCID 58312838HCID 58312838, compoundYield 58.7%

Procedure

A 2-dram round-bottomed vial was charged with (Z)-3-((tert-butoxycarbonyl)amino)-3-(1-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)piperidin-4-yl)propanoic acid, prepared using the general displacement procedure, (25 mg, 0.052 mmol), DMF (1 mL), DIPEA (34.9 μL, 0.209 mmol, 4 equiv.), and (3-(trifluoromethoxy)phenyl)methanamine (7.85 μL, 0.052 mmol, 1 equiv.). The reaction mixture was shaken for 20 minutes then HBTU (29.8 mg, 0.079 mmol, 1.5 equiv.) was added and the reaction mixture was shaken at RT for 3 h. The solvent was removed under reduced pressure (Genevac HT-4) and the resulting solid was washed with water (2×1 mL) and dried under high vacuum to provide 20 mg of (Z)-tert-butyl (1-(1-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrimidin-2-yl)piperidin-4-yl)-3-oxo-3-((3-(trifluoromethoxy)benzyl)amino)propyl)carbamate (20 mg, 34.1 mg theoretical, 58.7%).

Workup

  1. customprepared
  2. stirringthe reaction mixture was shaken at RT for 3 h
  3. customThe solvent was removed under reduced pressure (Genevac HT-4)
  4. washthe resulting solid was washed with water (2×1 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-95ee2e040bce4e708319642d40ff2b4f
Source dataset
uspto-grants-2013_10
Patent number
US08563539B2

Reaction notes

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