Ammonium Chloride → Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(isoquinolin-4-ylamino)pyridin-2-ylamino)cyclohexylcarbamate

HRID 1620117Notes

Reaction equation

HRID 1620117 reaction equation
[Cl-].[NH4+].CC[N:5]=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[C:34]([O:38][C:39]([NH:41][C@H:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C@H:43]1[NH:48][C:49]1[C:57]([F:58])=[CH:56][C:52]([C:53]([OH:55])=O)=[C:51]([NH:59][C:60]2[C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH:63]=[N:62][CH:61]=2)[N:50]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(OCC)(=O)C.CN(C=O)C.O>[NH2:5][C:53]([C:52]1[CH:56]=[C:57]([F:58])[C:49]([NH:48][C@H:43]2[CH2:44][CH2:45][CH2:46][CH2:47][C@H:42]2[NH:41][C:39](=[O:40])[O:38][C:34]([CH3:36])([CH3:37])[CH3:35])=[N:50][C:51]=1[NH:59][C:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:63]=[N:62][CH:61]=1)=[O:55]

Participants

9

Reactant 5

HCID 25517Ammonium Chloride2×HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866838886-(cis-2-(Tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid

Product 1

HCID 86683889Tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(isoquinolin-4-ylamino)pyridin-2-ylamino)cyclohexylcarbamateYield 72.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ammonium chloride (28 mg), WSC.HCl (75 mg), HOBt.H2O (60 mg), and diisopropylethylamine (180 μl) were added to a DMF (1.3 ml) suspension containing 6-(cis-2-(tert-butoxycarbonylamino)cyclohexylamino)-5-fluoro-2-(isoquinoline 4-ylamino)nicotinic acid (65 mg), followed by stirring at room temperature for 3 hours. A saturated aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture. Solid matter was collected by filtration and washed with water and ethyl acetate, and a light yellow solid of tert-butyl cis-2-(5-aminocarbonyl-3-fluoro-6-(isoquinolin-4-ylamino)pyridin-2-ylamino)cyclohexylcarbamate (47 mg) was thus obtained.

Workup

  1. filtrationSolid matter was collected by filtration
  2. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-ce3d70a12c5443b1b40295487ec72dfa
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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