Cyclopropanecarbonyl chloride → HCID 86619944, compound

HRID 1852550Notes

Reaction equation

HRID 1852550 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH2:22][CH2:21][CH2:20]NC3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.C1(C(Cl)=[O:27])CC1>C(Cl)Cl>[N:1]1([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH:17]3[CH:21]([CH:20]=[O:27])[CH2:22]3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 69309708HCID 69309708, compound

Product 1

HCID 86619944HCID 86619944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To DCM (8 mL) was added (4-benzotriazol-1-yl-pyrimidin-2-yl)-piperidin-3-ylamine (0.15 g), cyclopropylformyl chloride (40.5 μL) and TEA (0.285 mL), and the mixture stirred at RT. The product was purified by column chromatography on silica, using 100% DCM to 10% MeOH/DCM, then recrystallized from EtOAc to provide [3-(4-benzotriazol-1-yl-pyrimidin-2-ylamino)]-cyclopropylmethanone. Mp=99.0-100.0° C., 1H nmr (300 MHz, DMSO-d6): δ ppm 0.54-0.82 (m, 4H), 1.40-1.77 (m, 2H), 1.78-1.93 (m, 2H), 2.01-2.19 (m, 2H), 3.13 (t, J=11.11 Hz, 2H), 3.84-4.10 (m, 2H), 4.32 (d, J=11.68 Hz, 1H), 7.37 (d, J=5.27 Hz, 1H), 7.48-7.61 (m, 1H), 7.62-7.74 (m, 1H), 8.08-8.23 (d, 1H), 8.51 (d, J=5.27 Hz, 1H), 8.67 (d, J=8.29 Hz, 1H).

Workup

  1. customThe product was purified by column chromatography on silica
  2. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-e4a75a4261b34168a76e000283ac563a
Source dataset
uspto-grants-2015_02
Patent number
US08962622B2

Reaction notes

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