Triphenylphosphine → N-(4-chloro-3-(1-(3-(dimethylamino)propyl)-1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide

HRID 2098047Notes

Reaction equation

HRID 2098047 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:15][C:16]1[C:17]([C:40]2[N:44]=[CH:43][NH:42][N:41]=2)=[C:18]([NH:21][C:22](=[O:39])[CH2:23][N:24]2[C:33]3[C:28](=[CH:29][C:30]([C:34]([F:37])([F:36])[F:35])=[CH:31][CH:32]=3)[CH:27]=[CH:26][C:25]2=[O:38])[S:19][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:64][N:65]([CH3:70])[CH2:66][CH2:67][CH2:68]O>O1CCCC1>[Cl:15][C:16]1[C:17]([C:40]2[N:44]=[CH:43][N:42]([CH2:68][CH2:67][CH2:66][N:65]([CH3:70])[CH3:64])[N:41]=2)=[C:18]([NH:21][C:22](=[O:39])[CH2:23][N:24]2[C:33]3[C:28](=[CH:29][C:30]([C:34]([F:37])([F:36])[F:35])=[CH:31][CH:32]=3)[CH:27]=[CH:26][C:25]2=[O:38])[S:19][CH:20]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 766463-(Dimethylamino)-1-propanolHCID 178521249HCID 178521249, compound

Product 1

HCID 46869226N-(4-chloro-3-(1-(3-(dimethylamino)propyl)-1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.30 ml, 1.52 mmol) was added dropwise to a heterogeneous mixture of N-(4-chloro-3-(1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide (111 mg, 245 umol), polymer supported triphenylphosphine (500 mg, 1.50 mmol), and 3-(dimethylamino)propan-1-ol (300 mg, 2.91 mmol) in tetrahydrofuran (5 ml) at 0° C. After stirring for 2 h, the heterogeneous mixture was filtered through a pad of celite and concentrated under reduced pressure. The residue was purified by HPLC to yield N-(4-chloro-3-(1-(3-(dimethylamino)propyl)-1H-1,2,4-triazol-3-yl)thiophen-2-yl)-2-(2-oxo-6-(trifluoromethyl)quinolin-1(2H)-yl)acetamide. Method [7] Retention time 4.33 min by HPLC (M+=539 and 541). 1H NMR (300 MHz, DMSO-d6) δ 12.10 (s, 1H), 8.52 (s, 1H), 8.29 (s, 1H), 8.22 (d, J=9.6 Hz, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.72 (d, J=8.7, 1H), 7.18 (s, 1H), 6.87 (d, J=9.6 Hz, 1H), 5.32 (s, 2H), 4.31 (t, J=6.6 Hz, 2H), 3.09 (t, J=6.6 Hz, 2H), 2.75 (s, 6H), 2.17 (m, 2H).

Workup

  1. customat 0° C
  2. filtrationthe heterogeneous mixture was filtered through a pad of celite
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-b2af223220b840d783345e0b1145d965
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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