Methanesulfonyl chloride → HCID 56963255, compound

HRID 1037542Notes

Reaction equation

HRID 1037542 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]4[CH2:29][CH2:28][NH:27][CH2:26]4)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]([C:17]([NH:19][CH3:20])=[O:18])=[C:15]3[C:10]([CH:11]=[C:12]([N:24]([S:30]([CH3:33])(=[O:32])=[O:31])[CH:25]4[CH2:29][CH2:28][N:27]([S:44]([CH3:43])(=[O:46])=[O:45])[CH2:26]4)[C:13]([CH:21]4[CH2:23][CH2:22]4)=[CH:14]3)=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 56962531HCID 56962531, compound

Product 1

HCID 56963255HCID 56963255, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-bromophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)(pyrrolidin-3-yl)amino]-2H-indazole-3-carboxamide in DCM at 0° C. was added DIPEA (4 μL, 0.023 mmol), followed by methanesulfonyl chloride (3 μL, 0.039 mmol) and the mixture was stirred at RT for 20 min. The mixture was concentrated to dryness and purified by preparative LCMS (5-40-100% ACN in 0.1% aqueous formic acid) to afford Compound (52) as a white solid (1.4 mg, 36%). ESI-MS m/z calculated for [M+H]+: 610.1/612.1; found: 610.0/612.0; 1H NMR (400 MHz, CDCl3) δ 7.72 (2×s, 1H), 7.70-7.64 (m, 2H), 7.51-7.44 (m, 2H), 7.36 (2×s, J=2.6 Hz, 1H), 5.75 (2×d, J=5.0 Hz, 1H), 4.92-4.68 (m, 1H), 3.88-3.68 (m, 1H), 3.54-3.37 (m, 1H), 3.38-3.16 (m, 2H), 3.10 (d, J=4.6 Hz, 3H), 3.00 (2×d, 3H), 2.79 (2×s, 3H), 2.43-2.17 (m, 2H), 2.17-1.82 (m, 1H), 1.21-0.95 (m, 3H), 0.80-0.62 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. custompurified by preparative LCMS (5-40-100% ACN in 0.1% aqueous formic acid)

Sources & evidence

ORD record
ord-f6560b05ec894947aff5240daa55c0e1
Source dataset
uspto-grants-2013_10
Patent number
US08546389B2

Reaction notes

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