Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86676364, compound

HRID 1409681Notes

Reaction equation

HRID 1409681 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([C:14]([OH:16])=O)[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9]2)=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH2:32])=[S:31])=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:32][C:14]([C@@H:13]2[CH2:12][CH2:11][N:10]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9][C@H:8]2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:16])=[S:31])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27348264-ChlorothiobenzamideHCID 71237636HCID 71237636, compound

Product 1

HCID 86676364HCID 86676364, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (3R*,4R*)-3-(4-fluorophenyl)-1-phenethyl-piperidine-4-carboxylic acid (50 mg, 0.137 mmol, prepared according to the procedure disclosed in WO 2002/068387) and 4-chlorothiobenzamide (28.3 mg, 0.165 mmol) in CH2Cl2 (1.0 ml) was treated with HBTU (62.5 mg, 0.165 mmol) and DMAP (10 mg, 0.082 mmol) at rt. The mixture was stirred at rt for 6 h and then concentrated. The resulting residue was purified by RP-HPLC(C18, water, acetonitrile, 0.05% TFA) to afford the title compound, which was contaminated with 4-chlorothiobenzamide and was used in the next step without further purification. HPLC/MS: 481.3, 483.1 (M+1); Rt=1.14 (LC-2 HPLC conditions).

Workup

  1. customprepared
  2. concentrationconcentrated
  3. customThe resulting residue was purified by RP-HPLC(C18, water, acetonitrile, 0.05% TFA)

Sources & evidence

ORD record
ord-2a2b5844ed6144bd942891d819036e0d
Source dataset
uspto-grants-2014_12
Patent number
US08921394B2

Reaction notes

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