Acetonitrile → HCID 69411921, compound

HRID 1766388Notes

Reaction equation

HRID 1766388 reaction equation
[C:1]([N:20]1[CH2:24][C@@H:23]2[C@H:25]([NH2:28])[CH2:26][CH2:27][C@@H:22]2[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1([O:35][C:36](=O)[NH:37][C:38]2[CH:43]=[C:42]([C:44]3[N:48]([CH3:49])[N:47]=[N:46][N:45]=3)[CH:41]=[C:40]([CH2:50][CH3:51])[CH:39]=2)C=CC=CC=1.C(N(CC)CC)C.C(#N)C>CN(C)C=O>[CH2:50]([C:40]1[CH:39]=[C:38]([NH:37][C:36]([NH:28][CH:25]2[CH:23]3[CH:22]([CH2:21][N:20]([C:1]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:24]3)[CH2:27][CH2:26]2)=[O:35])[CH:43]=[C:42]([C:44]2[N:48]([CH3:49])[N:47]=[N:46][N:45]=2)[CH:41]=1)[CH3:51]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 22252693Phenyl 3-ethyl-5-(1-methyl-1H-tetraazol-5-yl)phenylcarbamateHCID 69413810HCID 69413810, compound

Product 1

HCID 69411921HCID 69411921, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3aR,4R,6aS)-2-trityloctahydrocyclopenta[c]pyrrol-4-amine (prepared following the procedures of Patent publication EP 0 359 172 A1; 250 mg, 678 μmol), [3-ethyl-5-(1-methyl-1H-tetrazol-5-yl)phenyl]-carbamic acid phenyl ester (219 mg, 678 μmol), triethylamine (189 μL, 1.36 mmol), acetonitrile (3 mL) and N,N-dimethylformamide (0.5 mL) was stirred at room temperature for 18.5 hours. The mixture was concentrated under vacuum, and the residue was dissolved in ethyl acetate. The solution was washed with 1.0 N aqueous sodium hydroxide, and the organic phase was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography, eluting with 40% ethyl acetate/hexane, to provide a white solid (353 mg, 87%). 1H NMR (300 MHz, CDCl3) δ8.04 (s, 1H), 7.67 (s, 1H), 7.53 (s, 1H), 7.46 (d, J=7 Hz, 6H), 7.18 (t, J=7 Hz, 6H), 7.07 (t, J=7 Hz, 3H), 6.97 (s, 1H), 6.11 (d, J=7 Hz, 1H), 4.04 (s, 3H), 2.74 (m, 1H), 2.6-2.4 (m, 4H), 2.4-2.1 (m, 3H), 1.91 (m, 1H), 1.8-1.7 (m, 3H), 1.58 (m, 1H), 1.12 (t, J=7 Hz, 3H).

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated under vacuum
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with 1.0 N aqueous sodium hydroxide
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-36b475ae443242bf8f84b12c46fae7e5
Source dataset
uspto-grants-2007_06
Patent number
US07230022B2

Reaction notes

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