Water → HCID 59456944, compound

HRID 1362224Notes

Reaction equation

HRID 1362224 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[CH2:10][C:9]2[CH:11]=[C:12](/[CH:15]=[CH:16]/[C:17]([N:19]([CH3:31])[CH2:20][C:21]3[S:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[C:22]=3[CH3:30])=[O:18])[CH:13]=[N:14][C:8]=2[NH:7][C:6]1=[O:32].C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[CH3:31][N:19]([CH2:20][C:21]1[S:25][C:24]2[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=2[C:22]=1[CH3:30])[C:17](=[O:18])/[CH:16]=[CH:15]/[C:12]1[CH:13]=[N:14][C:8]2[NH:7][C:6](=[O:32])[N:5]([CH2:4][CH:3]=[O:2])[CH2:10][C:9]=2[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 59456923HCID 59456923, compound

Product 1

HCID 59456944HCID 59456944, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-[3-(2,2-dimethoxy-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]-N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide (450 mg, 0.937 mmol) in CH2Cl2 (20 mL) was treated with TFA (1 mL) and H2O (1 mL). The reaction was allowed to stir overnight at room temperature. The solution was washed with saturated NaHCO3 (2×15 mL). The aqueous solutions were extracted with CH2Cl2 (40 mL). The combined CH2Cl2 solutions were washed with brine, dried over Na2SO4, and concentrated to give the title compound (440 mg, 99%) as a white solid and as amide rotomers: 1H NMR (300 MHz, DMSO-d6) δ 10.15 (s, 1H), 9.54 (s, 1H), 8.40 (s, 1H), 8.02 (s, 1H), 7.87 (d, J=7.5 Hz, 1H), 7.73 (d, J=7.8 Hz, 1H), 7.53-7.31 (m, 4H), 5.11-4.88 (m, 2H), 4.51 (s, 2H), 4.18 (s, 2H), 3.15-2.93 (m, 3H), 2.42 (s, 3H); MS (ESI) m/e 435 (M+H)+.

Workup

  1. washThe solution was washed with saturated NaHCO3 (2×15 mL)
  2. extractionThe aqueous solutions were extracted with CH2Cl2 (40 mL)
  3. washThe combined CH2Cl2 solutions were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cc8be5d3cdda4ee499a2537d278b3383
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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