Triethylamine → HCID 67087033, compound

HRID 2095549Notes

Reaction equation

HRID 2095549 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]([OH:22])=O)[C:14](=[O:23])[C@@H:13]2[CH3:24])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:25]1[C:27]2([CH2:32][CH2:31][NH:30][CH2:29][C@H:28]2[OH:33])[CH2:26]1.Cl.C1C2(CCNC[C@H]2O)C1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.OS([O-])(=O)=O.[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]([N:30]3[CH2:31][CH2:32][C:27]4([CH2:25][CH2:26]4)[C@H:28]([OH:33])[CH2:29]3)=[O:22])[C:14](=[O:23])[C@@H:13]2[CH3:24])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44541812(4S)-6-Azaspiro[2.5]octan-4-ol hydrochloride2×HCID 44541813(4S)-6-Azaspiro[2.5]octan-4-olHCID 67074220HCID 67074220, compound2×

Product 1

HCID 67087033HCID 67087033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.070 g (0.20 mmol) of 3-[(S)-4-(3,4-dichloro-phenylcarbamoyl)-3-methyl-2-oxo-piperazin-1-yl]-propionic acid (intermediate 12) in 1.5 ml of DMF was treated with 0.045 ml (0.28 mmol) of (S)-6-aza-spiro[2.5]octan-4-ol; hydrochloride (intermediate 2), 0.054 ml (0.40 mmol) of triethylamine and at 0° C. with 0.081 g (0.22 mmol) of HATU. Over night, the suspension was naturally warmed to RT, poured on aqueous 10% KHSO4 solution and extracted with EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried (Na2SO4) and evaporated to give after purification with flash chromatography (SiO2, dichloromethane/methanol 99:1 to 96:4) 0.069 g (70%) of the titled compound as white foam. MS: 483.2 (MH+, 2Cl).

Workup

  1. customat 0° C.
  2. waitOver night
  3. extractionextracted with EtOAc (3×)
  4. washThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give
  8. customafter purification with flash chromatography (SiO2, dichloromethane/methanol 99:1 to 96:4) 0.069 g (70%) of the titled compound as white foam

Sources & evidence

ORD record
ord-0435f287bad64e05b1c1470baafc652d
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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