Cyclopropanecarboxylic acid → HCID 58117700, compound

HRID 405938Notes

Reaction equation

HRID 405938 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.[CH2:16]1[C:22]2[CH:23]=[CH:24][C:25]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)=[CH:26][C:21]=2[CH2:20][CH2:19][NH:18][CH2:17]1>CN(C)C=O>[CH:1]1([C:4]([N:18]2[CH2:19][CH2:20][C:21]3[CH:26]=[C:25]([O:27][CH:28]4[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]4)[CH:24]=[CH:23][C:22]=3[CH2:16][CH2:17]2)=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 58117796HCID 58117796, compound

Product 1

HCID 58117700HCID 58117700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

16 l cyclopropylcarboxylic acid are placed in 3 ml dimethylformamide, then 174 l diisopropylethylamine and 93.1 mg O-(7-azabenzotriazol-1-yl-)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) are added. After 15 min 77.5 mg tert-butyl 4-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)-piperidine-1-carboxylate are added. The reaction mixture is stirred at ambient temperature until there is no further reaction and the product is purified directly by preparative HPLC (method B). 70 mg of the product are obtained as a solid. Analytical HPLC-MS (method D): RT=1.37 min.

Workup

  1. customno further reaction
  2. customthe product is purified directly by preparative HPLC (method B)

Sources & evidence

ORD record
ord-d1a98260e42e4f9bab7aa28a489625d6
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

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