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

HRID 72145Notes

Reaction equation

HRID 72145 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-589c675f5f1e4a23a292f586aad512f3
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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