HCID 57757929, compound → HCID 57758159, compound

HRID 229619Notes

Reaction equation

HRID 229619 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[C:9](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1>C(O)(=O)C.O=[Pt]=O>[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[C:9]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 57757929HCID 57757929, compound

Product 1

HCID 57758159HCID 57758159, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent3×

Procedure

A suspension of PtO2 (16 mg, 0.070 mmol) in acetic acid (0.5 ml) was added to a suspension of ethyl (2E)-3-[4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]acrylate (144 mg, 0.408 mmol) in acetic acid (2 ml) under N2 atmosphere. The flask was evacuated and refilled with hydrogen gas (3×) and the reaction proceeded under a hydrogen atmosphere (1 atm) for 1 d. Additional PtO2 (50 mg, 0.22 mmol) in acetic acid (0.5 ml) was added and the reaction proceeded under H2 atmosphere for an additional 1 d. The reaction was filtered through a Celite pad and washed with MeOH. It was evaporated to dryness, diluted with EtOAc and washed with aqueous Na2CO3. The aqueous layer was back extracted with EtOAc (2×). Organic was dried (Na2SO4), filtered, and evaporated to dryness to afford the above compound as a yellow solid (120 mg, yield 90%). 1H-NMR (CD3OD) δ 7.70 (s, 1H), 7.47 (s, 1H), 7.12 (d, J=8.3 Hz, 2H), 6.84 (d, J=8.3 Hz, 2H), 4.06 (q, J=7.8 Hz, 2H), 2.82 (t, J=7.8 Hz, 2H), 2.48 (t, J=7.7 Hz, 2H), 1.18(t, J=7.8 Hz, 3H); MS [M+H]+=326; LCMS RT=1.20 min.

Workup

  1. customThe flask was evacuated
  2. additionrefilled with hydrogen gas (3×)
  3. customfor 1 d
  4. filtrationThe reaction was filtered through a Celite pad
  5. washwashed with MeOH
  6. customIt was evaporated to dryness
  7. additiondiluted with EtOAc
  8. washwashed with aqueous Na2CO3
  9. extractionThe aqueous layer was back extracted with EtOAc (2×)
  10. dry with materialOrganic was dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-da4d19249a104e1d9df53c4737a60dc2
Source dataset
uspto-grants-2009_07
Patent number
US07563791B2

Reaction notes

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