Methanesulfonyl chloride → HCID 66884465, compound

HRID 72146Notes

Reaction equation

HRID 72146 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([NH:9][C:10]([N:12]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][N:19]=3)[CH2:13]1)=[O:11])[CH2:2]2.CCN(C(C)C)C(C)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl.CC(O)=O.CO>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:17][C@@H:14]2[CH2:15][CH2:16][N:12]([C:10]([NH:9][CH:3]3[CH2:4][CH:5]4[N:8]([S:36]([CH3:35])(=[O:38])=[O:37])[CH:1]([CH2:7][CH2:6]4)[CH2:2]3)=[O:11])[CH2:13]2)=[N:19][CH:20]=1)#[N:25]

Participants

7

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66884620HCID 66884620, compound

Product 1

HCID 66884465HCID 66884465, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 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 (18 mg, 0.053 mmol) and i-Pr2NEt (0.075 mL, 0.4 mmol) in CH2Cl2 (1 mL) was added methanesulfonyl chloride (0.008 mL, 0.10 mmol). The mixture was stirred overnight at rt, diluted with HOAc (0.1 mL) and MeOH (0.9 mL) and purified by prep HPLC to afford the title compound (13 mg, 58%). LC-MS Method 1 tR=1.1 min, m/z=419; 1H NMR (CD3OD) [selected resonances] 2.93 (s, 3H), 4.47 (m, 1H), 6.78 (d, 1H), 7.77 (d, 1H), 8.40 (s, 1H)

Workup

  1. custompurified by prep HPLC

Sources & evidence

ORD record
ord-ff74afed80d443a2bc589dd4fd90c2d2
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

Loading…