Cyclopropanecarbonyl chloride → HCID 89783582, compound

HRID 1056321Notes

Reaction equation

HRID 1056321 reaction equation
[NH2:1][C:2]1[C:3]([CH3:22])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([C:12]1[NH:20][C:19]3[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=3[CH:13]=1)[CH:8]=[CH:7][CH:6]=2.[CH:23]1([C:26](Cl)=[O:27])[CH2:25][CH2:24]1>C(Cl)Cl>[CH3:22][C:3]1[C:2]([NH:1][C:26]([CH:23]2[CH2:25][CH2:24]2)=[O:27])=[N:11][C:10]2[C:5]([N:4]=1)=[CH:6][CH:7]=[CH:8][C:9]=2[C:12]1[NH:20][C:19]2[CH2:18][CH2:17][NH:16][C:15](=[O:21])[C:14]=2[CH:13]=1

Participants

4

Reactant 2

HCID 77637Cyclopropanecarbonyl chlorideHCID 89783894HCID 89783894, compound

Product 1

HCID 89783582HCID 89783582, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-(3-amino-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (445a, 79 mg, 0.269 mmol) and TEA (0.18 mL, 1.34 mmol) in DCM (3 mL) was added cyclopropane carbonyl chloride (0.037 mL, 0.404 mmol). After the addition, the mixture was stirred at RT 24 h, concentrated, and purified on a silica gel column (0-10% MeOH/DCM) to give the title compound (55 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.47 (1H, br. s.), 10.52 (1H, br. s.), 8.05 (1H, d, J=7.6 Hz), 7.64 (1H, d, J=8.0 Hz), 7.54 (1H, t, J=7.8 Hz), 7.03 (1H, d, J=2.0 Hz), 6.93 (1H, br. s.), 3.43 (2H, td, J=6.7, 2.3 Hz), 2.89 (2H, t, J=6.8 Hz), 2.74 (3H, s), 2.21 (1H, br. s.), 0.95-1.04 (2H, m), 0.90 (2H, d, J=7.2 Hz). m/z (ESI, +ve) 362 (M+H)+.

Workup

  1. additionAfter the addition
  2. concentrationconcentrated
  3. custompurified on a silica gel column (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-3980a61e01f14df5bed1cdae5251d01f
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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