Diisopropylethylamine → 6-Cyclopropylmethoxy-5-piperidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amide

HRID 639312Notes

Reaction equation

HRID 639312 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[N:8][C:7]=2[N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:52][C@@H:53]([CH2:56][CH:57]([CH3:59])[CH3:58])[CH2:54][OH:55]>CN(C=O)C>[OH:55][CH2:54][C@@H:53]([NH:52][C:12]([C:10]1[CH:9]=[N:8][C:7]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)[N:11]=1)=[O:14])[CH2:56][CH:57]([CH3:59])[CH3:58]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 111307L-LeucinolHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 685679986-Cyclopropylmethoxy-5-piperidin-1-yl-pyrazine-2-carboxylic acid

Product 1

HCID 248312576-Cyclopropylmethoxy-5-piperidin-1-yl-pyrazine-2-carboxylic acid ((S)-1-hydroxymethyl-3-methyl-butyl)-amideYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11 mg (0.04 mmol) 6-cyclopropylmethoxy-5-piperidin-1-yl-pyrazine-2-carboxylic acid, 15.3 mg (0.048 mmol) TBTU, 15.3 mg (0.119 mmol) DIPEA and 7 mg (0.059 mmol) (S)-2-amino-4-methyl-pentan-1-ol (commercially available) in 1 mL DMF was shaken at room temperature for 16 h. The mixture was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The combined product fractions were evaporated to yield 10.5 mg (70%) of the title compound. m/z (ES+): 377.5 (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. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-853ea375a6774ddaba78ed9c0cd63124
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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