Hydrochloric Acid → HCID 68454023, compound

HRID 511864Notes

Reaction equation

HRID 511864 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[F:33][C:34]1([F:40])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.[F:41][C:42]([F:71])([F:70])[CH2:43][O:44][C:45]1[CH:46]=[CH:47][C:48]([C@H:51]([NH:53][C:54]([C@H:56]2[CH2:58][C@@H:57]2[C:59]2[CH:69]=[CH:68][C:62]([O:63][CH2:64][C:65](O)=[O:66])=[CH:61][CH:60]=2)=[O:55])[CH3:52])=[N:49][CH:50]=1.Cl>>[F:33][C:34]1([F:40])[CH2:39][CH2:38][N:37]([C:65](=[O:66])[CH2:64][O:63][C:62]2[CH:61]=[CH:60][C:59]([C@H:57]3[CH2:58][C@@H:56]3[C:54]([NH:53][C@@H:51]([C:48]3[CH:47]=[CH:46][C:45]([O:44][CH2:43][C:42]([F:41])([F:70])[F:71])=[CH:50][N:49]=3)[CH3:52])=[O:55])=[CH:69][CH:68]=2)[CH2:36][CH2:35]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 67289581HCID 67289581, compound

Product 1

HCID 68454023HCID 68454023, compoundYield 50.6%

Procedure

A mixture of HBTU (28 mg, 0.075 mmol), triethylamine (0.03 mL, 0.25 mmol), 4,4-difluoropiperidine hydrochloride (9.5 mg, 0.060 mmol) and 2-(4-((1S*,2S*)-2-(((R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)carbamoyl)cycl opropyl)phenoxy)acetic acid (28 mg, 0.050 mmol) was stirring for 4 hours at room temperature. The mixture was poured into 2 mol/l hydrochloric acid, and the aqueous layer was extracted with ethyl acetate, dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative LC-MS to give 13.7 mg (50% yield) of the title compound.

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-95e9dc3408b642288e585c09c474a5dd
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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