Triethylamine → HCID 42601577, compound

HRID 2093500Notes

Reaction equation

HRID 2093500 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.CN1[C:41](=[O:42])[CH2:40][CH2:39]C1.C(Cl)(=O)C=C>C(Cl)Cl>[O:22]([C:18]1[CH:17]=[C:16]([NH:15][C:13]2[N:12]=[CH:11][N:10]=[C:9]([NH:8][C:4]3[CH:3]=[C:2]([NH:1][C:41](=[O:42])[CH:40]=[CH2:39])[CH:7]=[CH:6][CH:5]=3)[CH:14]=2)[CH:21]=[CH:20][CH:19]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 13387N-methyl-2-pyrrolidoneHCID 57708307HCID 57708307, compound

Product 1

HCID 42601577HCID 42601577, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N4-(3-aminophenyl)-N6-(3-phenoxyphenyl)pyrimidine-4,6-diamine (40 mg, 0.1 mmol), Et3N (0.03 mL, 0.2 mmol) and NMP (0.4 mL) in CH2Cl2 (2 mL), at 0° C., was added acryloyl chloride (6) (29 mg, 0.3 mmol). The reaction mixture was allowed to come to rt and stirred at this temperature for 3 h. It was washed with 10% NaHCO3 solution (2 mL), water (2 mL), brine (2 mL) and dried over Na2SO4. Filtration followed by concentration under reduced pressure offered a residue which was purified by column chromatography (SiO2, 230-400, chloroform/methanol, 9/1) to gave N-(3-(6-(3-phenoxyphenylamino)pyrimidin-4-ylamino)phenyl)acrylamide (I-75) as a light brown solid. 1H NMR (DMSO-d6) δ ppm: 5.73 (dd, J=1.72 & 10 Hz, 1H), 6.18 (s, 1H), 6.24 (dd, J=1.92 & 17 Hz, 1H), 6.45 (dd, J=10.04 & 16.88 Hz, 1H), 6.54-6.57 (m, 1H), 7.01-7.05 (m, 2H), 7.11-7.15 (dd, J=0.88 & 7.48 Hz, 1H), 7.19-7.32 (s, 4H), 7.35-7.41 (m, 4H), 7.89 (s, 1H), 8.26 (s, 1H), 9.2 (s, 1H), 9.25 (s, 1H), 10.26 (s, 1H); LCMS: m/e 423.8 (M+1).

Workup

  1. customto come to rt
  2. washIt was washed with 10% NaHCO3 solution (2 mL), water (2 mL), brine (2 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration
  5. concentrationfollowed by concentration under reduced pressure
  6. customwas purified by column chromatography (SiO2, 230-400, chloroform/methanol, 9/1)

Sources & evidence

ORD record
ord-7ffaa0466c2b46a7a8af2259bee7a547
Source dataset
uspto-grants-2013_05
Patent number
US08445498B2

Reaction notes

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