Dimethylamine → HCID 67343604, compound

HRID 536684Notes

Reaction equation

HRID 536684 reaction equation
F[B-](F)(F)F.N1(O[C:16](N(C)C)=[N+:17](C)[CH3:18])C2C=CC=CC=2N=N1.C(O)(=O)C1C=CC=CC=1.[N:32]1[C:36]2[CH:37]=[CH:38][C:39]([C:41]([N:43]3[CH2:50][CH2:49][C@:48]4([CH3:53])[C@H:51]([CH3:52])[C@H:44]3[CH2:45][C:46]3[CH:57]=[CH:56][C:55]([C:58]([OH:60])=O)=[CH:54][C:47]=34)=[O:42])=[CH:40][C:35]=2[NH:34][CH:33]=1.C(N(C(C)C)C(C)C)C.CNC>CN(C)C=O>[CH3:16][N:17]([CH3:18])[C:58]([C:55]1[CH:56]=[CH:57][C:46]2[CH2:45][C@@H:44]3[C@@H:51]([CH3:52])[C@:48]([CH3:53])([C:47]=2[CH:54]=1)[CH2:49][CH2:50][N:43]3[C:41]([C:39]1[CH:38]=[CH:37][C:36]2[N:32]=[CH:33][NH:34][C:35]=2[CH:40]=1)=[O:42])=[O:60]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67346012HCID 67346012, compound

Product 1

HCID 67343604HCID 67343604, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (90 mg) is added to a solution of (2R,6R,11S)-3-(3H-benzoimidazole-5-carbonyl)-6,11-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocine-8-carboxylic acid benzoic acid (0.10 g) and ethyldiisopropylamin (53 μL) in dimethylformamide (2 mL). The resulting solution is stirred at ambient temperature for 20 min before dimethylamine (40% in H2O, 60 μL) is added. The solution is stirred overnight. The mixture is concentrated under reduced pressure and the residue is purified by HPLC on reversed phase (H2O/MeCN/NH3) to give the product as a solid.

Workup

  1. additionis added
  2. concentrationThe mixture is concentrated under reduced pressure
  3. customthe residue is purified by HPLC on reversed phase (H2O/MeCN/NH3)

Sources & evidence

ORD record
ord-e7dfe3374c6d4232b7a31113cffa64ef
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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