Diisopropylethylamine → HCID 24993204, compound

HRID 1664735Notes

Reaction equation

HRID 1664735 reaction equation
Cl.[NH2:2][C:3]1([C:6]#[N:7])[CH2:5][CH2:4]1.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:51]1[C:53]2([CH2:58][CH2:57][N:56]([C:59]([NH:61][C@@H:62]([CH2:66][C:67]([F:76])([F:75])[CH2:68][C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[C:63](O)=[O:64])=[O:60])[CH2:55][CH2:54]2)[CH2:52]1>CN(C=O)C>[C:6]([C:3]1([NH:2][C:63]([C@@H:62]([NH:61][C:59]([N:56]2[CH2:55][CH2:54][C:53]3([CH2:51][CH2:52]3)[CH2:58][CH2:57]2)=[O:60])[CH2:66][C:67]([F:75])([F:76])[CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[O:64])[CH2:5][CH2:4]1)#[N:7]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 57946196HCID 57946196, compound

Product 1

HCID 24993204HCID 24993204, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13.3 mg of 1-aminocyclopropanecarbonitrile hydrochloride (1.0 eq.), 15.2 mg of HOAt (1.0 eq.), 57 μl of DIPEA (3 eq.) and 42.5 mg of HATU (1.0 eq.) were added successively to a solution of 41.0 mg of (S)-2-[(6-azaspiro[2.5]octane-6-carbonyl)amino]-4,4-difluoro-5-phenylpentanoic acid (0.11 mmol) in 5 ml of DMF. The reaction mixture was stirred at RT for 4 h and then concentrated under reduced pressure. The residue thus obtained was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA). The product-containing fractions were combined and freeze-dried. In this way, N—[(S)-1-(1-cyanocyclopropylcarbamoyl)-3,3-difluoro-4-phenylbutyl]-6-azaspiro[2.5]octane-6-carboxamide was obtained as a colorless amorphous solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue thus obtained
  3. customwas purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA)
  4. customfreeze-dried

Sources & evidence

ORD record
ord-fcae467f22af4614b34c3dce817c3094
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Reaction notes

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