Dimethylformamide → (2R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-(2-(4-chlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)propanoate

HRID 1161213Notes

Reaction equation

HRID 1161213 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[C:14]([O:16][CH3:17])=[O:15])[C:7]2=[O:12].CN(C)C=O.C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[Cl:65][C:66]1[CH:71]=[CH:70][C:69]([CH:72]([CH3:76])[C:73](O)=[O:74])=[CH:68][CH:67]=1>>[Si:20]([O:19][CH2:18][C@@H:13]([N:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[NH:1][C:73](=[O:74])[CH:72]([C:69]2[CH:70]=[CH:71][C:66]([Cl:65])=[CH:67][CH:68]=2)[CH3:76])[C:7]1=[O:12])[C:14]([O:16][CH3:17])=[O:15])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 102525DL-2-(4-chlorophenyl)propanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67087826(R)-Methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate

Product 1

HCID 70842291(2R)-Methyl 3-(tert-butyldimethylsilyloxy)-2-(5-(2-(4-chlorophenyl)propanamido)-1-oxoisoquinolin-2(1H)-yl)propanoate

Procedure

A round bottom flask was charged with (R)-methyl 2-(5-amino-1-oxoisoquinolin-2(1H)-yl)-3-(tert-butyldimethylsilyloxy)propanoate (500 mg, 0.001 mol), N,N-dimethylformamide (2 mL, 0.03 mol), N,N-diisopropylethylamine (0.5 mL, 0.003 mol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (1 g, 0.003 mol) and 2-(4-chlorophenyl)propanoic acid (340 mg, 0.0018 mol) and the reaction stirred at room temperature overnight then for another 12 h. The solvent was removed and the residue purified by flash chromatography to yield the product as a white solid. MS m/z=545.4 (M+H).

Workup

  1. waitfor another 12 h
  2. customThe solvent was removed
  3. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-0011d0573681439197ab1d2579a85ff7
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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