5-Aminoisoquinoline → HCID 11200436, compound

HRID 559486Notes

Reaction equation

HRID 559486 reaction equation
[C:1](OC(OC(OC(C)(C)C)=O)=O)(OC(C)(C)C)=[O:2].[F:19][C:20]([F:34])([F:33])[C:21]1[CH:22]=[CH:23][C:24]([N:27]2[CH2:31][CH2:30][C@@H:29]([NH2:32])[CH2:28]2)=[N:25][CH:26]=1.[NH2:35][C:36]1[CH:45]=[CH:44][CH:43]=[C:42]2[C:37]=1[CH:38]=[CH:39][N:40]=[CH:41]2>C(Cl)Cl>[CH:41]1[C:42]2[C:37](=[C:36]([NH:35][C:1]([NH:32][C@@H:29]3[CH2:30][CH2:31][N:27]([C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:33])[F:34])=[CH:26][N:25]=4)[CH2:28]3)=[O:2])[CH:45]=[CH:44][CH:43]=2)[CH:38]=[CH:39][N:40]=1

Participants

5

Reactant 3

HCID 707665-AminoisoquinolineHCID 11401990HCID 11401990, compoundHCID 11780301diBoc-carbonate

Product 1

HCID 11200436HCID 11200436, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of di-tert-butyl tricarbonate, (0.681 g, 2.595 mmol), in dry DCM (1 ml) was added a solution of D2, (0.5 g, 2.162 mmol) in dry DCM (1 ml) in one portion. After the initial effervescence, the solution was stirred at room temperature for 0.3 h. A solution of 5-aminoisoquinoline, (0.312 g, 2.162 mmol) in dry DCM (1 ml) was added. The reaction mixture was stirred at room temperature overnight. The resultant precipitate was removed by centrifugation, and the solid washed with ether and dried to give the title compound as a white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customThe resultant precipitate was removed by centrifugation
  3. washthe solid washed with ether
  4. customdried

Sources & evidence

ORD record
ord-7c9f2eee478d4b2580d23be4d1c1de3b
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

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