Diisopropylethylamine → HCID 67343374, compound

HRID 1257738Notes

Reaction equation

HRID 1257738 reaction equation
[CH:1]1([CH2:4][C:5]([OH:7])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH:41]1[C:53]2[CH:52]([CH2:54][O:55][C:56]([N:58]3[CH2:63][CH2:62][CH2:61][CH:60]([NH:64][C:65]4[C:70]([NH2:71])=[CH:69][N:68]=[C:67]5[N:72]([S:75]([C:78]6[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=6)(=[O:77])=[O:76])[CH:73]=[CH:74][C:66]=45)[CH2:59]3)=[O:57])[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]=2[CH:44]=[CH:43][CH:42]=1>CN(C=O)C>[CH:41]1[C:53]2[CH:52]([CH2:54][O:55][C:56]([N:58]3[CH2:63][CH2:62][CH2:61][CH:60]([NH:64][C:65]4[C:70]([NH:71][C:5](=[O:7])[CH2:4][CH:1]5[CH2:2][CH2:3]5)=[CH:69][N:68]=[C:67]5[N:72]([S:75]([C:78]6[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=6)(=[O:77])=[O:76])[CH:73]=[CH:74][C:66]=45)[CH2:59]3)=[O:57])[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:45]=2[CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 138440Cyclopropaneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67346331HCID 67346331, compound

Product 1

HCID 67343374HCID 67343374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Cyclopropylacetic acid (0.300 g, 3.00 mmol), HATU (1.14 g, 3.00 mmol), and diisopropylethylamine (0.627 ml, 3.60 mmol) were added sequentially to a solution of 3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (1.78 g, 3.00 mmol) in DMF (50 ml) at 25° C. The reaction mixture was stirred for 1.5 h at 25° C., then was concentrated under reduced pressure. The residue was partitioned between half-saturated NaHCO3 (125 ml) and EtOAc (2×150 ml). The combined organic layers were dried over Mg2SO4, filtered, and the filtrate was concentrated under reduced pressure to give crude 3-[1-benzenesulfonyl-5-(2-cyclopropyl-acetylamino)-1H-pyrrolo[2,3-b]pyridin-4-ylamino]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester as a brown foam. LCMS (Method G, ESI): RT=1.24 min, m+H=676.4. This material was used in the next step below without additional purification or characterization.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between half-saturated NaHCO3 (125 ml) and EtOAc (2×150 ml)
  3. dry with materialThe combined organic layers were dried over Mg2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d2aff32551b45959a13fbd799690dc1
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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