N-BOC-ethylenediamine → HCID 59320870, compound

HRID 341177Notes

Reaction equation

HRID 341177 reaction equation
N1([C:6](C2C=CN=C2)=[O:7])C=CN=C1.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][N:23]3[C:26]([C:29]4[CH:30]=[C:31]([NH2:35])[CH:32]=[CH:33][CH:34]=4)=[CH:27][N:28]=[C:22]3[CH:21]=2)=[CH:16][CH:15]=1.[C:36]([O:40][C:41](=[O:46])[NH:42][CH2:43][CH2:44][NH2:45])([CH3:39])([CH3:38])[CH3:37]>C1COCC1>[C:36]([O:40][C:41](=[O:46])[NH:42][CH2:43][CH2:44][NH:45][C:6]([NH:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:26]2[N:23]3[CH:24]=[CH:25][C:20]([C:17]4[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=4)=[CH:21][C:22]3=[N:28][CH:27]=2)[CH:30]=1)=[O:7])([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 3

HCID 187201N-BOC-ethylenediamineHCID 59277797HCID 59277797, compoundHCID 68595120HCID 68595120, compound

Product 1

HCID 59320870HCID 59320870, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazol-1-yl-(3H-pyrrol-3-yl)-methanone (240 mg, 1.5 mmol) was added to a stirred solution of 3-[7-(4-fluoro-phenyl)-imidazo[1,2-a]pyridin-3-yl]phenylamine (450 mg, 1.5 mmol) in THF (10 ml) at 0° C. under N2. The mixture was stirred at this temperature for 2 hours and then at RT for 3 hours. Half of the reaction mixture was transferred to a separate flask and treated with (2-amino-ethyl)-carbamic acid tert-butyl ester (320 mg, 2 mmol). The mixture was stirred at RT for 16 hours. The volatiles were removed in vacuo and the residue was purified using silica chromatography (2→4% 2M NH3-MeOH/CH2Cl2) to give the title compound (85 mg, foam). MS: [M+H]+ 490.

Workup

  1. waitat RT for 3 hours
  2. customHalf of the reaction mixture was transferred to a separate flask
  3. stirringThe mixture was stirred at RT for 16 hours
  4. customThe volatiles were removed in vacuo
  5. customthe residue was purified

Sources & evidence

ORD record
ord-1b7fc167172240d59883ac01a5ad9a4c
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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