Methanesulfonyl chloride → HCID 67117743, compound

HRID 914240Notes

Reaction equation

HRID 914240 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:37])[C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([NH:15][C:16]3[N:17]=[CH:18][C:19]4[N:25]([CH3:26])[C:24](=[O:27])[C:23]([F:29])([F:28])[CH2:22][N:21]([CH:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)[C:20]=4[N:35]=3)=[CH:9][C:8]=2F)[CH2:2]1.CCN(C(C)C)C(C)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49]>C(Cl)Cl>[CH:30]1([N:21]2[CH2:22][C:23]([F:28])([F:29])[C:24](=[O:27])[N:25]([CH3:26])[C:19]3[CH:18]=[N:17][C:16]([NH:15][C:10]4[CH:9]=[CH:8][C:7]([C:6]([NH:5][CH:3]5[CH2:4][N:1]([S:48]([CH3:47])(=[O:50])=[O:49])[CH2:2]5)=[O:37])=[CH:12][C:11]=4[O:13][CH3:14])=[N:35][C:20]2=3)[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 57955666HCID 57955666, compound

Product 1

HCID 67117743HCID 67117743, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(azetidin-3-yl)-4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-2-fluoro-5-methoxybenzamide (100 mg, 0.19 mmol) in DCM (2.5 mL, 1:2:2) was added DIEA (50 μL, 0.285 mmol), followed by methanesulfonyl chloride (23 μL, 0.21 mmol). After stirring overnight the solvent was removed and the product purified by reverse phase HPLC, free based, and lyophilized to yield a white solid (9.3 mg, 9%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.54-1.79 (m, 6H) 1.96 (br. s., 2H) 3.05 (s, 3H) 3.92 (s, 3H) 3.94 (d, J=1.77 Hz, 2H) 4.03-4.15 (m, 4H) 4.61-4.72 (m, 1H) 4.76-4.87 (m, 1H) 7.24 (d, J=6.57 Hz, 1H) 8.08 (s, 1H) 8.27 (d, 1H) 8.31 (s, 1H) 8.73 (d, J=3.79 Hz, 1H). [M+H] calc'd for C25H30F3N7O5S, 598. found 598.

Workup

  1. customwas removed
  2. customthe product purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a155e4ad8c0e4bd7a250f833e64793bf
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

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