1,2-Dichloroethane → HCID 68926778, compound

HRID 32083Notes

Reaction equation

HRID 32083 reaction equation
OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[N:15]1([CH2:21][C:22]2[CH:23]=[C:24]3[C:29](=[CH:30][CH:31]=2)[CH2:28][CH:27]([NH2:32])[CH2:26][CH2:25]3)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[S:43]([NH:46][CH:47]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:48][C:49](O)=[O:50])(=[O:45])=[O:44].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][C:34]=1[S:43]([NH:46][CH:47]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:48][C:49]([NH:32][CH:27]1[CH2:26][CH2:25][C:24]2[C:29](=[CH:30][CH:31]=[C:22]([CH2:21][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:23]=2)[CH2:28]1)=[O:50])(=[O:45])=[O:44]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 36326413-(naphthalene-2-sulfonamido)-3-phenylpropionic AcidHCID 1317270586-Piperidin-1-ylmethyl-1,2,3,4-tetrahydro-naphthalen-2-ylamine bis-TFA salt

Product 1

HCID 68926778HCID 68926778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Piperidin-1-ylmethyl-1,2,3,4-tetrahydro-naphthalen-2-ylamine bis-TFA salt (Step F) (0.143 g, 0.327 mmol), 3-(naphthalen-2-yl-sulfonylamino)-3-phenyl-propionic acid (0.128 g, 0.360 mmol), HOBt (0.057 g, 0.425 mmol) and EDC (0.081 g, 0.425 mmol) were dissolved in CH2Cl2 (25 mL) and stirred at RT. TEA (0.228 mL, 1.64 mmol) was added drop-wise to the mixture and the reaction was stirred at RT until HPLC analysis showed complete consumption of starting material. The reaction mixture was diluted with CH2Cl2 and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the crude material. The crude was purified by flash column chromatography to furnish the title compound. MS (APCI pos) 582 (M+H).

Workup

  1. stirringthe reaction was stirred at RT until HPLC analysis
  2. customconsumption of starting material
  3. additionThe reaction mixture was diluted with CH2Cl2
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford the crude material
  8. customThe crude was purified by flash column chromatography

Sources & evidence

ORD record
ord-cfe0b86a3ba34e5a980b4a09dc919254
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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