HCID 86605445, compound → HCID 58192966, compound

HRID 1645186Notes

Reaction equation

HRID 1645186 reaction equation
C([O:5][C:6](=O)[NH:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([S:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[N+:31]([O-:33])=[O:32])=[CH:13][N:14]2[CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[N:22][CH:23]=2)=[CH:10][CH:9]=1)(C)(C)C>C(O)=O>[N+:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[S:24][C:12]1[C:11]2[C:15](=[CH:16][C:8]([NH:7][CH:6]=[O:5])=[CH:9][CH:10]=2)[N:14]([CH2:17][C:18]2[CH:23]=[N:22][CH:21]=[N:20][CH:19]=2)[CH:13]=1)([O-:33])=[O:32]

Participants

3

Reactant 1

HCID 86605445HCID 86605445, compound

Product 1

HCID 58192966HCID 58192966, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

[3-(2-Nitro-phenylsulfanyl)-1-pyrimidin-5-ylmethyl-1H-indol-6-yl]-carbamic acid tert-butyl ester (3.8 g, 8.0 mmol) was dissolved in 150 mL of formic acid and stirred for 4 hours. The solution was concentrated in vacuo. NaHCO3-sat was added and the mixture was extracted with CH2Cl2 (2×) The combined organic layers were washed with brine and dried over Na2SO4. The solution was allowed to stand overnight. The formed solid was filtered affording a mixture of compound 118 and structure 23 of Scheme VII, where R1=3,5-pyrimidyl, R2=2-nitrophenyl, R3═R4═H (2.4 g).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionNaHCO3-sat was added
  3. extractionthe mixture was extracted with CH2Cl2 (2×) The combined organic layers
  4. washwere washed with brine
  5. dry with materialdried over Na2SO4
  6. waitto stand overnight
  7. filtrationThe formed solid was filtered
  8. customaffording

Sources & evidence

ORD record
ord-7533da8f068e45bbb548a8d0fc7cf223
Source dataset
uspto-grants-2012_02
Patent number
US08124647B2

Reaction notes

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