2-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amine → HCID 178454061, compound

HRID 1366741Notes

Reaction equation

HRID 1366741 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:13]([O:17][C:18]([NH:20][C@H:21]1[CH2:26][CH2:25][C@H:24](OS(C)(=O)=O)[CH2:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC>C(#N)C>[C:13]([O:17][C:18](=[O:19])[NH:20][C@H:21]1[CH2:22][CH2:23][C@@H:24]([O:12][C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[C:2]([NH2:1])=[N:3][CH:4]=[CH:5]3)[CH2:25][CH2:26]1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 1357539911-Aminoisoquinolin-6-olHCID 178418975HCID 178418975, compound

Product 1

HCID 178454061HCID 178454061, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 1-amino-6-hydroxyisoquinoline (0.08 g, 0.5mmol), methane-sulfonic acid trans-4-tert-butoxycarbonylaminocyclohexyl ester (176 mg) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (270mg, ˜2.2 mmol/g loading) in acetonitrile (2ml) were heated at 120° C. over a period of 15 minutes using the microwave. The excess supported reagent was removed by filtration, washing with acetonitrile followed by methanol, and the filtrate evaporated to dryness under reduced pressure. Purification was achieved by prep-HPLC to give cis-[4-(1-aminoisoquinolin-6-yloxy)cyclohexyl]carbamic acid tert-butyl ester (14 mg).

Workup

  1. customwas removed by filtration
  2. washwashing with acetonitrile
  3. customthe filtrate evaporated to dryness under reduced pressure
  4. customPurification

Sources & evidence

ORD record
ord-9d1c99598d674130a6e7095968db9a33
Source dataset
uspto-grants-2011_02
Patent number
US07893088B2

Reaction notes

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