Ammonia → HCID 66599640, compound

HRID 1944141Notes

Reaction equation

HRID 1944141 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:19]([NH:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH:28]=[N:27][CH:26]=[CH:25]3)=[O:20])[CH2:10][NH:11]C(=O)OC(C)(C)C)=[CH:5][CH:4]=1.[ClH:32].N>C1COCC1.O.CO>[ClH:32].[ClH:32].[NH2:11][CH2:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1)[C:19]([NH:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[N:27][CH:26]=[CH:25]2)=[O:20]

Participants

7

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 59563703HCID 59563703, compound

Product 1

HCID 66599640HCID 66599640, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 2-(4-(hydroxymethyl)phenyl)-3-(isoquinolin-6-ylamino)-3-oxopropylcarbamate (E139) in THF and water and cooled to 0° C. was added HCl (1 N in Et2O). After 30 min the mixture was warmed to room temperature and the solution was stirred for 48 h. 2 M NH3 in MeOH was added. The solvents were evaporated and the mixture purified by column chromatography (SiO2, 0-5-10% (2 M NH3 in MeOH)/CH2Cl2). The compound was dissolved in DCM/MeOH and 1 N HCl in Et2O added. The solvents were evaporated to give pure 3-amino-2-(4-(hydroxymethyl)phenyl)-N-(isoquinolin-6-yl)propanamide dihydrochloride (E144).

Workup

  1. customThe solvents were evaporated
  2. customthe mixture purified by column chromatography (SiO2, 0-5-10% (2 M NH3 in MeOH)/CH2Cl2)
  3. dissolutionThe compound was dissolved in DCM/MeOH
  4. addition1 N HCl in Et2O added
  5. customThe solvents were evaporated

Sources & evidence

ORD record
ord-025889d0e4444867b744493f78bb37a5
Source dataset
uspto-grants-2013_03
Patent number
US08394826B2

Reaction notes

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