Methanesulfonyl chloride → N-({4-[8-Amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-3-yl]cyclohexyl}methyl)methanesulfonamide

HRID 2042357Notes

Reaction equation

HRID 2042357 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[C:8]2[N:9]([C:13]([C@H:25]3[CH2:30][CH2:29][C@H:28]([CH2:31][NH2:32])[CH2:27][CH2:26]3)=[N:14][C:15]=2[C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=[CH:11][N:12]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:6][C:7]1[C:8]2[N:9]([C:13]([CH:25]3[CH2:26][CH2:27][CH:28]([CH2:31][NH:32][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:29][CH2:30]3)=[N:14][C:15]=2[C:16]2[NH:17][C:18]3[C:23]([CH:24]=2)=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=[CH:11][N:12]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178511226HCID 178511226, compound

Product 1

HCID 16678351N-({4-[8-Amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-3-yl]cyclohexyl}methyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (4.40 μL, 0.057 mmol was added to a mixture of 1-{trans-4-[8-amino-1-(1H-indol-2-yl)imidazo[1,5-a]pyrazin-3-yl]cyclohexyl}methanamine (20.5 mg, 0.057 mol) and PS-DIEA (3.90 mmol/g loading; 60 mg, 0.2 mmol) in DCM (1.14 mL). The reaction mixture was stirred for 30 min at r.t. for 18 h. The crude reaction mixture was then concentrated and residue purified by mass directed preparative HPLC to afford 4 mg of desired product. MS (ES+): m/z 439.10 (100) [MH+]. 1H NMR (CD3OD, 400 MHz): δ 8.24 (br s, 2H), 7.61 (m, 2H), 7.46 (dd, J=8.4, 0.8 Hz, 1H), 7.19 (ddd, J=7.2, 1.2, 1.2 Hz, 1H), 7.08 (ddd, J=7.2, 1.2, 1.2 Hz, 1H), 6.75 (d, J=0.8 Hz, 1H), 3.14 (m, 1H), 2.07 (m, 4H), 1.85 (m, 2H), 1.64 (m, 1H), 1.26 (m, 2H).

Workup

  1. customThe crude reaction mixture
  2. concentrationwas then concentrated
  3. customresidue purified by mass

Sources & evidence

ORD record
ord-5bc76f71f6124c00938ff16afa9d764b
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

Loading…