Ammonia → HCID 68294248, compound

HRID 1850066Notes

Reaction equation

HRID 1850066 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:42]([C:51]1[S:52][CH:53]=[C:54](/[CH:56]=[CH:57]/[C:58](O)=[O:59])[N:55]=1)[CH:43]=[CH:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.N>C(Cl)Cl.CO>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:17][C:58](=[O:59])/[CH:57]=[CH:56]/[C:54]1[N:55]=[C:51]([CH2:42][CH:43]=[CH:44][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[S:52][CH:53]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68294157HCID 68294157, compound

Product 1

HCID 68294248HCID 68294248, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

DIPEA (0.21 g, 0.54 mmol), o-phenylene diamine (39 mg, 0.36 mmol) and HATU (89 mg, 0.23 mmol) were added to a solution of (E)-3-(2-cinnamylthiazol-4-yl)acrylic acid (50 mg, 0.18 mmol) in DCM (20 mL) and the reaction mixture was stirred overnight at room temperature under nitrogen. After completion of the reaction as indicated by HPLC, the reaction mixture was washed with saturated NaHCO3 and brine. The organic layer was then dried (Na2SO4) and evaporated to give the crude product. Repeated silica gel column chromatography using a 0-10% gradient of MeOH, containing 0.1% NH3 in DCM gave pure (E)-N-(2-aminophenyl)-3-(2-cinnamylthiazol-4-yl)acrylamide (26 mg) as a tan-colored solid. ES+ (M+H)+362. 1H NMR (CD3OD) δ: 7.66 (s, 1H), 7.60 (d, J=15.4 Hz, 1H), 7.39-7.45 (m, 2H), 7.27-7.35 (m, 2H), 7.20 (dd, J=8.0, 1.4 Hz, 1H), 7.17-7.26 (m, 1H), 7.04 (ddd, J=8.0, 7.7, 1.4 Hz, 1H), 7.05 (d, J=15.3 Hz, 1H), 6.87 (dd, J=8.0, 1.4 Hz, 1H), 6.74 (td, J=7.7, 1.4 Hz, 1H), 6.66 (dt, J=15.9, 1.1 Hz, 1H), 6.47 (dt, J=15.9, 6.9 Hz, 1H), 3.95 (dd, J=6.9, 1.1 Hz, 2H)

Workup

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed with saturated NaHCO3 and brine
  3. dry with materialThe organic layer was then dried (Na2SO4)
  4. customevaporated
  5. customto give the crude product

Sources & evidence

ORD record
ord-e5e7346eef1949cca9be5a2fefcd5a88
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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