1-Naphthalenemethanamine → HCID 68852007, compound

HRID 1726957Notes

Reaction equation

HRID 1726957 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[NH2:20][C:21]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][CH2:29][CH:28]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:27]2)[N:23]([CH2:40][C:41]#[C:42][CH3:43])[C:22]=1[C:44](OCC)=[O:45].[C:49]1([CH2:59][NH2:60])[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51][CH:50]=1>COCCOC>[C:49]1([CH2:59][N:60]2[C:44](=[O:45])[C:22]3[N:23]([CH2:40][C:41]#[C:42][CH3:43])[C:24]([N:26]4[CH2:31][CH2:30][CH2:29][CH:28]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:27]4)=[N:25][C:21]=3[NH:20][C:2]2=[O:4])[C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51][CH:50]=1

Participants

6

Reactant 4

HCID 83551-NaphthalenemethanamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 67268813HCID 67268813, compound

Product 1

HCID 68852007HCID 68852007, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

0.5 g triphosgene and 1.4 ml triethylamine are added successively to an ice-cooled solution of 2.0 g of ethyl 5-amino-2-(3-tert-butoxycarbonylamino-piperidin-1-yl)-3-(but-2-ynyl)-3H-imidazole-4-carboxylate in 35 ml dry 1,2-dimethoxyethane. After 2 h stirring at ambient temperature 0.76 ml naphth-1-ylmethylamine and a further 35 ml dry 1,2-dimethoxyethane are added. The reaction solution is stirred for a further 14 h at ambient temperature. Then the solution is evaporated down to approx. 20 ml and diluted with 150 ml dichloromethane. The organic phase is washed with 1 M hydrochloric acid and with aqueous sodium hydrogen carbonate solution and then dried over sodium sulphate. After the solvent has been eliminated the residue is dissolved in 100 ml of ethanol and combined with 0.41 g sodium ethoxide. The solution is stirred for 4 h at 60° C. After cooling to ambient temperature the reaction solution is neutralised with 1 M hydrochloric acid and the ethanol is evaporated off. Water is added and the precipitate is separated off, washed with ether and dried at 60° C.

Workup

  1. customThen the solution is evaporated down to approx. 20 ml
  2. additiondiluted with 150 ml dichloromethane
  3. washThe organic phase is washed with 1 M hydrochloric acid and with aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulphate
  5. dissolutionis dissolved in 100 ml of ethanol
  6. stirringThe solution is stirred for 4 h at 60° C
  7. temperatureAfter cooling to ambient temperature the reaction solution
  8. customthe ethanol is evaporated off
  9. additionWater is added
  10. customthe precipitate is separated off
  11. washwashed with ether
  12. customdried at 60° C.

Sources & evidence

ORD record
ord-00b145de76e34eedb1b779253f49ba5d
Source dataset
uspto-grants-2009_02
Patent number
US07495003B2

Reaction notes

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