3,4-Dimethylaniline → HCID 66965792, compound

HRID 1514944Notes

Reaction equation

HRID 1514944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[N:10]([O:21][CH2:22][CH3:23])[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18](O)=[O:19])[CH:12]=2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:55][C:56]1[CH:57]=[C:58]([CH:60]=[CH:61][C:62]=1[CH3:63])[NH2:59]>CN(C=O)C.C(OCC)(=O)C>[CH3:55][C:56]1[CH:57]=[C:58]([NH:59][C:18]([C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:9]([C:3]4[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[N:10]3[O:21][CH2:22][CH3:23])=[CH:15][CH:14]=2)=[O:19])[CH:60]=[CH:61][C:62]=1[CH3:63]

Participants

7

Reactant 4

HCID 72483,4-DimethylanilineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66965296HCID 66965296, compound

Product 1

HCID 66965792HCID 66965792, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2,6-dichlorophenyl)-1-ethoxy-1H-indole-6-carboxylic acid (230 mg, 660 μmol) in DMF (5 mL) was added HATU (375 mg, 990 μmol), triethylamine (137 μL, 99 mg, 980 μmol) and 3,4-dimethylaniline (80 mg, 660 μmol). After stirring the mixture for 72 h at ambient temperature, the solution was poured into ethyl acetate and extracted with water once and brine five times. The organic layer was dried, filtered, and solvent removed under reduced pressure. The residual material was chromatographed with a 10-60% gradient of heptane/ethyl acetate to afford 2-(2,6-dichlorophenyl)-1-ethoxy-1H-indole-6-carboxylic acid (3,4-dimethylphenyl)-amide. 1H NMR (DMSO-d6, 400 MHz): δ 10.16 (s, 1H), 8.19 (s, 1H), 7.71 (m, 4H), 7.58 (m, 3H), 7.12 (d, J=8.2 Hz, 1H), 6.60 (s, 1H), 4.14 (q, J=7.1 Hz, 2H), 2.24 (s, 3H), 2.21 (s, 3H), 1.12 (t, J=7.1 Hz, 3H). MS (m/z) 453.0 (M+1); Retention time=1.72 min (Method 10). Anal. Calcd.: C, 66.23; H, 4.89; N, 6.18. Found: C, 66.34; H, 4.97; N, 6.06.

Workup

  1. extractionextracted with water once
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customsolvent removed under reduced pressure
  5. customThe residual material was chromatographed with a 10-60% gradient of heptane/ethyl acetate

Sources & evidence

ORD record
ord-9937ef0b417d4617aee7d589d14b01a4
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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