Dichloromethane → ethyl 4-{[(1S,4S)-4-isopropyl-4-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopent-2-en-1-yl]amino}-3-methoxypiperidine-1-carboxylate

HRID 643729Notes

Reaction equation

HRID 643729 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=O)[CH2:7][CH2:6][N:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4]1.C(Cl)Cl.[CH:18]([C@@:21]1([C:27]([N:29]2[CH2:34][CH2:33][N:32]([C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[CH:37][N:36]=3)[CH2:31][CH2:30]2)=[O:28])[CH2:25][C@H:24]([NH2:26])[CH:23]=[CH:22]1)([CH3:20])[CH3:19].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:18]([C@@:21]1([C:27]([N:29]2[CH2:30][CH2:31][N:32]([C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:38]=[CH:37][N:36]=3)[CH2:33][CH2:34]2)=[O:28])[CH2:25][C@H:24]([NH:26][CH:8]2[CH2:7][CH2:6][N:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4][CH:3]2[O:2][CH3:1])[CH:23]=[CH:22]1)([CH3:20])[CH3:19]

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 2724451Ethyl 3-methoxy-4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 68484653HCID 68484653, compound

Product 1

HCID 59263093ethyl 4-{[(1S,4S)-4-isopropyl-4-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopent-2-en-1-yl]amino}-3-methoxypiperidine-1-carboxylate

Procedure

The title compound was prepared by taking ethyl 3-methoxy-4-oxopiperidine-1-carboxylate (148 mg, 0.000737 mol) in Methylene chloride (3 mL, 0.04 mol) and adding (1S,4S)-4-isopropyl-4-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopent-2-en-1-amine (0.31 g, 0.00081 mol;), Triethylamine (0.8 mL, 0.006 mol;) and Sodium triacetoxyborohydride (0.312 g, 0.00147 mol). The reaction was stirred overnight. The reaction was quenched with (20 mL) NaOH and extracted with (3×10 mL) CH2Cl2. The organic layers were collected, dried over MgSO4 and concentrated in vacuo. The crude was taken on to the next step as-is (410 mg, 98%). MS calculated for C28H40F3N5O4: (M+H) 568; found 568.1.

Workup

  1. customThe reaction was quenched with (20 mL) NaOH
  2. extractionextracted with (3×10 mL) CH2Cl2
  3. customThe organic layers were collected
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0c7c566142d84bf080e2a75548c841c8
Source dataset
uspto-grants-2010_04
Patent number
US07700624B2

Reaction notes

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