Hydrochloric Acid → Hydrochloric Acid

HRID 2200286Notes

Reaction equation

HRID 2200286 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([NH:51][C:52]([CH3:66])([CH3:65])[CH2:53][CH:54]([C:58]1[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=1)[C:55](O)=[O:56])=O)(C)(C)C.Cl>C(Cl)Cl>[NH2:51][C:52]([CH3:66])([CH3:65])[CH2:53][CH:54]([C:58]1[CH:59]=[CH:60][C:61]([Cl:64])=[CH:62][CH:63]=1)[C:55]([N:40]1[CH2:39][CH2:38][N:37]([C:35]2[C:36]3[C@H:28]([CH3:27])[CH2:29][C@@H:30]([OH:43])[C:31]=3[N:32]=[CH:33][N:34]=2)[CH2:42][CH2:41]1)=[O:56].[ClH:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 666178284-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acidHCID 66618034(5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochloride

Product 2

HCID 313Hydrochloric AcidYield 615.7%HCID 59670868HCID 59670868, compound

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 4-(tert-butoxycarbonylamino)-2-(4-chlorophenyl)-4-methylpentanoic acid (33 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 dissolved in ethyl acetate (50 mL) and washed with brine (5×50 mL). The organic phase was dried and concentrated to afford the product. The product was treated with HCl to afford 4-amino-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-4-methylpentan-1-one as HCl salt (22 mg, 49%).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with brine (5×50 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customto afford the product

Sources & evidence

ORD record
ord-eb3b405c03b04144a95636fef40c9b5d
Source dataset
uspto-grants-2016_06
Patent number
US09359340B2

Reaction notes

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