Ethyl orthoformate → HCID 178519352, compound

HRID 2272169Notes

Reaction equation

HRID 2272169 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:12]2[C@@H:11]3[C@@H:6]([N:7]([C:15]([C:17]4[CH:25]=[CH:24][C:20]5[NH:21][CH:22]=[N:23][C:19]=5[CH:18]=4)=[O:16])[CH2:8][CH2:9][CH2:10]3)[CH2:5][C:4]=2[C:3]=1O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:39](OCC)(OCC)[O:40]CC>CO>[NH:21]1[C:20]2[CH:24]=[CH:25][C:17]([C:15]([N:7]3[C@H:6]4[C@H:11]([C:12]5[CH:13]=[C:14]6[O:40][CH:39]=[N:1][C:2]6=[CH:3][C:4]=5[CH2:5]4)[CH2:10][CH2:9][CH2:8]3)=[O:16])=[CH:18][C:19]=2[N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 178507262HCID 178507262, compound

Product 1

HCID 178519352HCID 178519352, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (cis-7-amino-8-hydroxy-2,3,4,4a,9,9a-hexahydro-indeno[2,1-b]pyridin-1-yl)-(1H-benzoimidazol-5-yl)-methanone (100 mg), 4-toluenesulfonic acid hydrate (5 mg), triethyl orthoformate (40 μL), and methanol (1 mL) is stirred at 60° C. for 2 h. After cooling to room temperature, the mixture is concentrated and the residue is dissolved in ethyl acetate. The resulting solution is washed with 1 M NaOH solution, dried (Na2SO4), and concentrated to give the title compound. Yield: 50 mg (49% of theory); LC (method 1): tR=2.24 min; Mass spectrum (ESI+): m/z=359 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture is concentrated
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe resulting solution is washed with 1 M NaOH solution
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-92ba322ba9f54a408295e2b244190b3e
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

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