HCID 68687232, compound → HCID 68687483, compound

HRID 1441335Notes

Reaction equation

HRID 1441335 reaction equation
[F:1][C:2]1[C:3]([C:24]2[N:28]([CH:29]([CH3:31])[CH3:30])[C:27]([CH3:32])=[N:26][CH:25]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][CH2:18][C@H:17]([NH:20]C(=O)C)[CH2:16]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1>C(O)(C)C.O.Cl>[NH2:20][C@H:17]1[CH2:18][CH2:19][N:15]([C:12]2[CH:11]=[CH:10][C:9]([NH:8][C:5]3[N:4]=[C:3]([C:24]4[N:28]([CH:29]([CH3:30])[CH3:31])[C:27]([CH3:32])=[N:26][CH:25]=4)[C:2]([F:1])=[CH:7][N:6]=3)=[CH:14][CH:13]=2)[CH2:16]1

Participants

5

Reactant 1

HCID 68687232HCID 68687232, compound

Product 1

HCID 68687483HCID 68687483, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

N-[(3S)-1-(4-{[5-Fluoro-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidin-2-yl]amino}phenyl)pyrrolidin-3-yl]acetamide (Example 152; 0.49 g, 1.12 mmol) in isopropanol (20 ml), water (5 ml) and hydrochloric acid (2 ml) was heated at reflux under nitrogen for 18 hours. After evaporation under reduced pressure, the mixture was dissolved in water (15 ml) and adjusted to pH 9 with aqueous ammonium hydroxide solution. The solution was extracted with DCM (3×15 ml), dried and after evaporation under reduced pressure to give the title compound as a solid (0.42 g, 95%). NMR: 1.38 (d, 6H), 1.61-1.73 (m, 1H), 2.00-2.13 (m, 1H), 2.44 (s, 3H), 2.80-2.88 (m, 1H), 3.12-3.20 (m, 1H), 3.20-3.42 (m, 2H), 3.49-3.60 (m, 1H), 5.40-5.51 (m, 1H), 6.46 (d, 2H), 7.30 (d, 2H), 7.33 (s, 1H), 8.40 (s, 1H), 9.00 (s, 1H); m/z 396.

Workup

  1. temperatureat reflux under nitrogen for 18 hours
  2. customAfter evaporation under reduced pressure
  3. dissolutionthe mixture was dissolved in water (15 ml)
  4. extractionThe solution was extracted with DCM (3×15 ml)
  5. customdried
  6. customafter evaporation under reduced pressure

Sources & evidence

ORD record
ord-28f6dc9a73c34ad0a4f008d9724e8bae
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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