Diisopropylethylamine → HCID 57414216, compound

HRID 1918230Notes

Reaction equation

HRID 1918230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][NH:11][CH2:10][C@@:9]2([N:14]([CH3:25])[C:15](=[O:24])[O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH3:13])=[CH:4][CH:3]=1.[C:26]([N:31]1[CH2:36][CH2:35][CH:34]([C:37](O)=[O:38])[CH2:33][CH2:32]1)(=[O:30])[CH:27]([CH3:29])[CH3:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[F:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][C:15](=[O:24])[N:14]([C@:9]2([CH3:13])[C@@H:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][N:11]([C:37]([CH:34]3[CH2:33][CH2:32][N:31]([C:26](=[O:30])[CH:27]([CH3:28])[CH3:29])[CH2:36][CH2:35]3)=[O:38])[CH2:10]2)[CH3:25])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 167709591-(2-Methylpropanoyl)piperidine-4-carboxylic acidHCID 68089233HCID 68089233, compound

Product 1

HCID 57414216HCID 57414216, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 34 mg (0.093 mmol) rac-4-fluorophenyl (3R,4S)-4-(4-chlorophenyl)-3-methylpyrrolidin-3-yl(methyl)carbamate, 14.9 mg (0.075)mmol 1-isobutyrylpiperidine-4-carboxylic acid, 34.2 (0.09 mmol) HATU and 58 mg (0.45 mmol) DIPEA in 2 mL DMF was shaken for 3 h at room temperature. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 26.8 (66%) of the title compound as light yellow viscous oil. MS m/e: 544.2 [M+H]+.

Workup

  1. customThe mixture was subjected to purification by preparative HPLC on reversed phase
  2. washeluting with a gradient
  3. customformed from acetonitrile, water and NEt3
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions 26.8 (66%) of the title compound as light yellow viscous oil

Sources & evidence

ORD record
ord-ae54d9241f3f45a3ba5064736bc4a7fe
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

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