Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide

HRID 554936Notes

Reaction equation

HRID 554936 reaction equation
FC1C=CC(C[N:7]2C(=O)N(C3SC(C(O)=O)=C(C)N=3)C=N2)=CC=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[F:48][C:49]1[CH:71]=[CH:70][C:52]([CH2:53][N:54]2[C@@H:58]([CH3:59])[CH2:57][N:56]([C:60]3[S:61][C:62]([C:66]([OH:68])=O)=[C:63]([CH3:65])[N:64]=3)[C:55]2=[O:69])=[CH:51][CH:50]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>>[F:48][C:49]1[CH:71]=[CH:70][C:52]([CH2:53][N:54]2[C@@H:58]([CH3:59])[CH2:57][N:56]([C:60]3[S:61][C:62]([C:66]([NH2:7])=[O:68])=[C:63]([CH3:65])[N:64]=3)[C:55]2=[O:69])=[CH:51][CH:50]=1

Participants

5

Reactant 4

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 579198022-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acidHCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57919782(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamideYield 67%

Procedure

Following the procedure as described in Example 1, making variations as required to replace 2-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylic acid and 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (H BTU) with (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU), the title compound was obtained as a colorless solid in 67% yield: mp 192-194° C. (ethyl acetate/diethyl ether); 1H NMR (300 MHz, DMSO-d6) δ 7.40-7.32 (m, 4H), 7.18 (dd, J=8.8, 8.8 Hz, 2H), 4.59 (d, J=15.6 Hz, 1H), 4.30 (d, J=15.6 Hz, 1H), 4.18 (dd, J=10.0, 9.1 Hz, 1H), 3.79-3.68 (m, 1H), 3.54 (dd, J=10.0, 6.8 Hz, 1H), 2.45 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.5, 161.5 (d, 1JC-F=243 Hz), 157.3, 154.9, 150.7, 133.1 (d, 4JC-F=3 Hz), 129.9 (d, 3JC-F=8 Hz), 118.5, 115.4 (d, 2JC-F=2, Hz), 49.4, 48.6, 43.7, 18.4, 17.0; MS (ES+) m/z 348.8 (M+1).

Sources & evidence

ORD record
ord-52f373ace11c4522bed06f939bcc55f5
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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