Diisopropylethylamine → HCID 86726790, compound

HRID 1499567Notes

Reaction equation

HRID 1499567 reaction equation
[NH2:1][C:2]1[C:3]([C:16]([OH:18])=O)=[N:4][C:5]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[F:15])=[CH:6][N:7]=1.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.[C:52]([O:55][CH:56]1[C:60]2=[N:61][CH:62]=[C:63]([NH2:79])[C:64]([N:65]3[CH2:70][CH2:69][CH2:68][C@H:67]([NH:71][C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[CH2:66]3)=[C:59]2[CH2:58][CH2:57]1)(=[O:54])[CH3:53]>ClCCCl>[C:52]([O:55][CH:56]1[C:60]2=[N:61][CH:62]=[C:63]([NH:79][C:16]([C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]4[C:9]([F:15])=[CH:10][CH:11]=[CH:12][C:13]=4[F:14])[N:4]=3)=[O:18])[C:64]([N:65]3[CH2:70][CH2:69][CH2:68][C@H:67]([NH:71][C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[CH2:66]3)=[C:59]2[CH2:58][CH2:57]1)(=[O:54])[CH3:53]

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 867266943-Amino-4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetateHCID 867267893-Amino-6-(2,6-difluorophenyl)-2-pyrazinecarboxylic acid

Product 1

HCID 86726790HCID 86726790, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a pre-stirred solution of 3-amino-6-(2,6-difluorophenyl)pyrazine-2-carboxylic acid (18 mg, 0.070 mmol), HATU (32 mg, 0.084 mmol), and DIPEA (36 μL, 0.21 mmol) in 1,2-dichloroethane (0.3 mL) was added a solution of 3-amino-4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (38 mg, 0.097 mmol) in 1,2-dichloroethane (0.5 mL). The resulting solution was stirred at ambient temperature for 3 h. The crude reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (20 g silica gel column, eluting with 0-10% MeOH in DCM) to afford the sub-title compound (18 mg, 41%). LC/MS (ESI) calc. for C31H36F2N2O5(M+H)+: m/z=624.3. found: 624.1.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (20 g silica gel column, eluting with 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-18cfd600d341417590dfadff81e21408
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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