Ammonia → HCID 67345133, compound

HRID 536690Notes

Reaction equation

HRID 536690 reaction equation
C(N(CC)CC)C.C(O[C:12](=[O:14])[CH3:13])(=O)C.[NH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]2[C:27]3([CH3:31])[C:28]([CH3:30])([CH3:29])[CH:23]([N:24]([C:32]([C:34]4[CH:42]=[CH:41][C:37]5[N:38]=[CH:39][NH:40][C:36]=5[CH:35]=4)=[O:33])[CH2:25][CH2:26]3)[CH2:22][C:21]=2[CH:43]=1.N>C(#N)C.CO>[N:38]1[C:37]2[CH:41]=[CH:42][C:34]([C:32]([N:24]3[CH2:25][CH2:26][C:27]4([CH3:31])[C:28]([CH3:30])([CH3:29])[CH:23]3[CH2:22][C:21]3[CH:43]=[C:17]([CH2:16][NH:15][C:12](=[O:14])[CH3:13])[CH:18]=[CH:19][C:20]=34)=[O:33])=[CH:35][C:36]=2[NH:40][CH:39]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67345574HCID 67345574, compound

Product 1

HCID 67345133HCID 67345133, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

Triethylamine (38 μL) and acetic anhydride (26 μL) are added to a suspension of (9-aminomethyl-6,11,11-trimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl)-(3H-benzoimidazol-5-yl)-methanone (0.10 g) in acetonitrile (2 mL). The resulting mixture is stirred at ambient temperature for 1 h. Then, methanol (1 mL) and concentrated aqueous ammonia solution (0.5 mL) are added and the resulting solution is stirred for another 30 min. The solution is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (water/MeCN) to give the title compound as a white foam-like solid.

Workup

  1. stirringthe resulting solution is stirred for another 30 min
  2. concentrationThe solution is concentrated under reduced pressure
  3. customthe residue is purified by HPLC on reversed phase (water/MeCN)

Sources & evidence

ORD record
ord-0c5d8534ef4a4773b652c1d42f3f240b
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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