Diisopropylethylamine → HCID 71112313, compound

HRID 1409750Notes

Reaction equation

HRID 1409750 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.[N:32]1([C:37]2[N:42]=[CH:41][C:40]([C:43]([OH:45])=O)=[CH:39][N:38]=2)[CH:36]=[CH:35][N:34]=[CH:33]1.[CH:46]1([NH:49][CH:50]2[CH2:55][CH2:54][N:53]([C:56]3[O:60][N:59]=[C:58]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[N:57]=3)[CH2:52][CH2:51]2)[CH2:48][CH2:47]1>CN(C)C=O>[CH:46]1([N:49]([CH:50]2[CH2:51][CH2:52][N:53]([C:56]3[O:60][N:59]=[C:58]([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[N:57]=3)[CH2:54][CH2:55]2)[C:43]([C:40]2[CH:41]=[N:42][C:37]([N:32]3[CH:36]=[CH:35][N:34]=[CH:33]3)=[N:38][CH:39]=2)=[O:45])[CH2:48][CH2:47]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 55252176HCID 55252176, compoundHCID 68289604N-cyclopropyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-4-amine

Product 1

HCID 71112313HCID 71112313, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (75 mg) and ethyldiisopropylamine (74 μL) are added to a solution of 2-imidazol-1-yl-pyrimidine-5-carboxylic acid (40 mg) in N,N-dimethylformamide (5 mL) at room temperature. The solution is stirred for 10 min prior to the addition of cyclopropyl-[1-(3-phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-yl]amine (60 mg). The resulting mixture is stirred at 60° C. for 3 h, cooled to room temperature over night, and concentrated in vacuo. The crude product is purified by HPLC(H2O/MeOH/TFA). LC (method 1): tR=1.50 min; Mass spectrum (ESI+): m/z=457 [M+H]+.

Workup

  1. stirringThe resulting mixture is stirred at 60° C. for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe crude product is purified by HPLC(H2O/MeOH/TFA)

Sources & evidence

ORD record
ord-a62561cd50cc4e71a49ea1bb20c8f791
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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