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

HRID 2076564Notes

Reaction equation

HRID 2076564 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 L, 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, 2M, 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-8ebf2fdafeeb46179a17f4c85c9a26c4
Source dataset
uspto-grants-2011_04
Patent number
US07923555B2

Reaction notes

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