Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → Hydrochloric Acid

HRID 532777Notes

Reaction equation

HRID 532777 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[ClH:25].Cl.[CH3:27][C@H:28]1[C:36]2[C:35]([N:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[N:34][CH:33]=[N:32][C:31]=2[C@H:30]([OH:43])[CH2:29]1.C(OC([N:51]([CH:65]([CH3:67])[CH3:66])[CH2:52][C:53]([C:58]1[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=1)([OH:57])[C:54](O)=[O:55])=O)(C)(C)C>C(Cl)Cl>[Cl:64][C:61]1[CH:60]=[CH:59][C:58]([C:53]([OH:57])([CH2:52][NH:51][CH:65]([CH3:66])[CH3:67])[C:54]([N:40]2[CH2:39][CH2:38][N:37]([C:35]3[C:36]4[C@H:28]([CH3:27])[CH2:29][C@@H:30]([OH:43])[C:31]=4[N:32]=[CH:33][N:34]=3)[CH2:42][CH2:41]2)=[O:55])=[CH:63][CH:62]=1.[ClH:25]

Participants

6

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66618034(5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochlorideHCID 666183113-(Tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)-2-hydroxypropanoic acid

Product 2

HCID 313Hydrochloric AcidYield 615.7%HCID 596711622-(4-chlorophenyl)-2-hydroxy-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

HBTU (37 mg, 0.098 mmol) was added to a solution of (5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride (30 mg, 0.098 mmol) and 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)-2-hydroxypropanoic acid (35 mg, 0.098 mmol) in DCM (5 mL) and TEA (1 mL). The mixture was stirred at room temperature for 1 hour. The solvent was removed, and the residue was subject to column chromatography, eluted by DCM/MeOH (40:1). The resulting product was treated with HCl (4M, 2 mL) to afford 2-(4-chlorophenyl)-2-hydroxy-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-(isopropylamino)propan-1-one as HCl salt (22 mg, 48%).

Workup

  1. customThe solvent was removed
  2. washeluted by DCM/MeOH (40:1)
  3. additionThe resulting product was treated with HCl (4M, 2 mL)

Sources & evidence

ORD record
ord-7970db16df074749ba4cae3877fd94a0
Source dataset
uspto-grants-2014_10
Patent number
US08853199B2

Reaction notes

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