5-Aminoisoquinoline → 1-Cyclopentyl-3-(isoquinolin-5-yl)urea

HRID 716636Notes

Reaction equation

HRID 716636 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.CCN(C(C)C)C(C)C.[N:21]([CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)=[C:22]=[O:23]>C(Cl)Cl>[CH:24]1([NH:21][C:22]([NH:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][N:2]=[CH:1]3)=[O:23])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 707665-AminoisoquinolineHCID 81531DiisopropylethylamineHCID 643500Cyclopentyl Isocyanate

Product 1

HCID 471931071-Cyclopentyl-3-(isoquinolin-5-yl)urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To isoquinolin-5-amine (0.23 g, 1.595 mmol) in DCM (5 mL) was added DIEA (0.557 mL, 3.19 mmol) and isocyanatocyclopentane (0.180 mL, 1.595 mmol). After 24 h, the reaction was quenched with H2O (15 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine (10 mL) and dried (MgSO4). The impure yellow solid was collected and was carried onto the next step. MS (ESI) m/z: 256 (M+H)+.

Workup

  1. customthe reaction was quenched with H2O (15 mL)
  2. extractionextracted with EtOAc (3×30 mL)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customThe impure yellow solid was collected

Sources & evidence

ORD record
ord-653c06f6ba4c4ca7a9ca7ff3fc3b868a
Source dataset
uspto-grants-2015_11
Patent number
US09192607B2

Reaction notes

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