Triethylamine → HCID 49839067, compound

HRID 1396029Notes

Reaction equation

HRID 1396029 reaction equation
[F:1][C:2]1([F:17])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][CH:12]3[CH2:16][CH2:15][NH:14][CH2:13]3)=[CH:10][C:4]=2[O:3]1.C(N(CC)CC)C.C1([O:31][C:32](=O)[NH:33][C:34]2[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=2)C=CC=CC=1>C(#N)C>[N:36]1[CH:37]=[CH:38][CH:39]=[C:34]([NH:33][C:32]([N:14]2[CH2:15][CH2:16][CH:12]([CH2:11][C:9]3[CH:8]=[CH:7][C:5]4[O:6][C:2]([F:1])([F:17])[O:3][C:4]=4[CH:10]=3)[CH2:13]2)=[O:31])[CH:35]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 66974054HCID 66974054, compound

Product 1

HCID 49839067HCID 49839067, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
35 °C

Procedure

To a solution consisting of 3-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-pyrrolidine (111 mg, 0.399 mmol), triethylamine (0.1 mL, 0.72 mmol) and acetonitrile (2 mL) was added pyridin-3-yl-carbamic acid phenyl ester (90.1 mg, 0.421 mmol). The mixture was heated at 35° C. for 18 h, cooled to rt and then concentrated. The crude residue was purified (FCC) to give the title compound (56 mg, 39%). MS (ESI): mass calcd. For C18H17F2N3O3, 361.12. m/z found, 362.2 [M+H]+. 1H NMR (CD3OD): 8.63-8.59 (m, 1H), 8.16-8.13 (m, 1H), 7.97-7.92 (m, 1H), 7.35-7.30 (m, 1H), 7.16-7.09 (m, 2H), 7.06-7.02 (m, 1H), 3.66-3.53 (m, 2H), 3.48-3.38 (m, 1H), 3.19-3.11 (m, 1H), 2.85-2.72 (m, 2H), 2.62-2.50 (m, 1H), 2.11-2.02 (m, 1H), 1.78-1.66 (m, 1H).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-9a1c1f5776ab4074bfc167c3e544fc78
Source dataset
uspto-grants-2014_12
Patent number
US08901111B2

Reaction notes

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