Dimethylformamide → HCID 69374769, compound

HRID 860999Notes

Reaction equation

HRID 860999 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[NH2:8].[C:10]([O:14][Na])([CH3:13])(C)C.[N+](C1C=CC(OC(=O)C=C[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]3[CH:42]=[C:43]([C:51]([S:54]([CH3:57])(=[O:56])=[O:55])([CH3:53])[CH3:52])[CH:44]=[C:45]4[C:50]=3[N:49]=[CH:48][CH:47]=[CH:46]4)[CH:36]=2)=CC=1)([O-])=O.[CH3:59]N(C=O)C>[NH4+].[Cl-]>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[NH:8][C:10](=[O:14])[CH:13]=[CH:59][C:33]1[CH:34]=[CH:29][C:30]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]3[CH:42]=[C:43]([C:51]([S:54]([CH3:57])(=[O:56])=[O:55])([CH3:52])[CH3:53])[CH:44]=[C:45]4[C:50]=3[N:49]=[CH:48][CH:47]=[CH:46]4)[CH:36]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 898884-Amino-3,5-dichloropyridineHCID 69584527HCID 69584527, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 69374769HCID 69374769, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 3,5-dichloro-pyridin-4-ylamine (1.5 eq.) in DMF (0.1M) was added t-BuONa (1.5 eq.). The mixture was stirred for 15 min then 3-{3′-[6-(1-methanesulfonyl-1-methyl-ethyl)-quinolin-8-yl]-biphenyl yl}-acrylic acid 4-nitro-phenyl ester (1.0 eq.) was added. The final mixture was stirred for 12 h, poured in saturated aqueous NH4Cl and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:EtOAc; 9:1 to 1:9 in 20 min) afforded the title compound as a yellow solid. 1H NMR (400 MHz, acetone-d6): δ 9.44 (br s, 1H), 8.97 (dd, 1H), 8.64 (s, 2H), 8.50 (dd, 1H), 8.33 (d, 1H), 8.26 (d, 1H), 8.11 (t, 1H), 7.87–7.77 (m, 7H), 7.65–7.60 (m, 2H), 7.09 (d, 1H), 2.81 (s, 3H), 2.04 (s, 6H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6697ec5516b246c2a332c18e06be1751
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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