Methanesulfonyl chloride → HCID 66884465, compound

HRID 1948717Notes

Reaction equation

HRID 1948717 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-96f667b645514239b86c1c6918e9c716
Source dataset
uspto-grants-2013_03
Patent number
US08399504B2

Reaction notes

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