Trimethylsilyl isocyanate → 3-((r)-3-(5-Cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxamide

HRID 1948716Notes

Reaction equation

HRID 1948716 reaction equation
Cl.Cl.[CH:3]12[NH:10][CH:7]([CH2:8][CH2:9]1)[CH2:6][CH:5]([NH:11][C:12]([N:14]1[CH2:18][CH2:17][C@@H:16]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=3)[CH2:15]1)=[O:13])[CH2:4]2.CCN(C(C)C)C(C)C.[Si]([N:41]=[C:42]=[O:43])(C)(C)C>C(Cl)Cl>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([NH:19][C@@H:16]2[CH2:17][CH2:18][N:14]([C:12]([NH:11][CH:5]3[CH2:6][CH:7]4[N:10]([C:42]([NH2:41])=[O:43])[CH:3]([CH2:9][CH2:8]4)[CH2:4]3)=[O:13])[CH2:15]2)=[N:21][CH:22]=1)#[N:27]

Participants

5

Reactant 3

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 66884619(3R)-N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride

Product 1

HCID 668834483-((r)-3-(5-Cyanopyridin-2-ylamino)pyrrolidine-1-carboxamido)-8-azabicyclo[3.2.1]octane-8-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3R)—N-(8-azabicyclo[3.2.1]octan-3-yl)-3-(5-cyanopyridin-2-ylamino)pyrrolidine-1-carboxamide dihydrochloride salt (17.5 mg, 0.042 mmol) and i-Pr2NEt (0.032 mL, 0.18 mmol) in CH2Cl2 (1 mL) was added Me3SiNCO (0.008 mL, 0.06 mmol). The mixture was stirred at overnight and concentrated. The residue was purified by prep HPLC to give two isomeric products.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by prep HPLC
  3. customto give two isomeric products

Sources & evidence

ORD record
ord-954f087d7c1243258553f62ebad77415
Source dataset
uspto-grants-2013_03
Patent number
US08399504B2

Reaction notes

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