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2-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amine → 3-(1-Amino-isoquinolin-6-yloxy)piperidin-1--carboxylic acid tert-butyl ester

HRID 1435964
Notes
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Reaction equation

HRID 1435964 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].NC1C2C(=CC(O)=CC=2)C=CN=1.C(OC(N1CCC[C@@H](OS(C)(=O)=O)C1)=O)(C)(C)C.CCN(P1(N(C)CCCN1)=NC(C)(C)C)CC>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21]([NH2:25])=[N:20][CH:19]=[CH:18]3)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 199900182-tert-butylimino-N,N-diethyl-1-methyl-1,3,2lambda5-diazaphosphinan-2-amineHCID 29939737(R)-1-N-Boc-3-methanesulfonyloxypiperidineHCID 68875514(S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl esterHCID 1357539911-Aminoisoquinolin-6-ol

Product 1

HCID 77563464
3-(1-Amino-isoquinolin-6-yloxy)piperidin-1--carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
160 °C

Procedure

For an alternate procedure for the preparation of (S)-3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester, a suspension of 1-amino-6-hydroxyisoquinoline (0.8 g, 5.0 mmol), (R)-3-methanesulfonyloxypiperidine-1-carboxylic acid tert-butyl ester (1.76 g) and 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine on polystyrene (3.4 g, −2.2 mmol/g loading) in acetonitrile (10 ml) were heated at 160° C. over a period of 15 minutes using the microwave. The excess supported regent was removed by filtration, washing with acetonitrile followed by methanol, and the filtrate evaporated to dryness under reduced pressure. Purification was achieved by chromatography on silica (eluent: 2-10% methanol in ethyl acetate) to afford (S) 3-(1-amino-isoquinolin-6-yloxy)piperidin-1-carboxylic acid tert-butyl ester (72 mg), El-MS: m/z=344.1 [M+H]+.

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-a9ac1a8cca5946bd8943abe5ba2d0eaa
Source dataset
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07618985B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes