Cyclopropanecarboxylic acid → HCID 90033903, compound

HRID 1754849Notes

Reaction equation

HRID 1754849 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH2:38]([O:45][C:46]([N:48]1[CH2:53][CH2:52][C:51]2[N:54]=[C:55]([NH2:57])[S:56][C:50]=2[CH:49]1[C:58]1[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=1[O:65][CH2:66][C:67]([O:69][CH2:70][CH3:71])=[O:68])=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[CH2:38]([O:45][C:46]([N:48]1[CH2:53][CH2:52][C:51]2[N:54]=[C:55]([NH:57][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:6])[S:56][C:50]=2[CH:49]1[C:58]1[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=1[O:65][CH2:66][C:67]([O:69][CH2:70][CH3:71])=[O:68])=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 90022235HCID 90022235, compound

Product 1

HCID 90033903HCID 90033903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopropanecarboxylic acid (5 μL, 60 μmol, 1 eq.) in DMF (5 mL), DIPEA (51 μL, 300 μmol, 5 eq.) and TBTU (19 mg, 60 μmol, 1 eq.) were added in sequence. The resulting solution was stirred at r.t. for 30 minutes. Then (±)-2-amino-4-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid benzyl ester (30 mg, 60 μmol, 1 eq.) was added and the resulting mixture was stirred at r.t. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give the title compound as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at r.t. for 18 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by prep
  4. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-57a0d6d849cc49b6b0ffbdf8d9fc13b2
Source dataset
uspto-grants-2015_10
Patent number
US09169270B2

Reaction notes

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