Hydrochloric Acid → HCID 67386734, compound

HRID 1027139Notes

Reaction equation

HRID 1027139 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15]2([CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[O:14][CH2:13][C@H:12]1[C:21](O)=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)=[O:28].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.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[C:15]2([CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[O:14][CH2:13][C@H:12]1[C:21](=[O:22])[NH:25][CH2:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)=[O:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 216392-Amino-1-(4-bromophenyl)ethanoneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58432549HCID 58432549, compound

Product 1

HCID 67386734HCID 67386734, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-1,8-Dioxa-4-aza-spiro[4.5]decane-3,4-dicarboxylic acid 4-benzyl ester (1.05 gm, 3.27 mmol) was dissolved in DMF (10 mL) and the HCl salt of 2-amino-1-(4-bromo-phenyl)-ethanone (0.8 gm, 3.21 mmol) and HATU (1.34 gm, 3.5 mmol) were added, followed by diisopropylethyl amine (1.33 gm, 10.27 mmol). The mixture was stirred at room temperature for 3 hours, and then added dropwise into saturated aqueous NaHCO3 solution with stirring. The solid that crashed out was filtered and dried followed by redissolving (DCM) and filtration through a silica plug (eluting with ethyl acetate). This afforded 1.3 gm (78%) of the desired product as beige solid. LCMS: 519.2 (M+2).

Workup

  1. stirringwith stirring
  2. filtrationThe solid that crashed out was filtered
  3. customdried
  4. dissolutionby redissolving
  5. filtration(DCM) and filtration through a silica plug (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-33f5dd081d7b4f2c9b7c6740d739a994
Source dataset
uspto-grants-2014_05
Patent number
US08729077B2

Reaction notes

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