Triethylamine → HCID 118307645, compound

HRID 530410Notes

Reaction equation

HRID 530410 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:13][C:14]1[CH:15]=[C:16]([NH:27][C:28]2[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=2)[CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH2:26])[CH:21]=2)[CH:19]=1>C(Cl)Cl>[CH3:13][C:14]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH:21]=2)[CH:17]=[C:16]([NH:27][C:28]2[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 90042012HCID 90042012, compound

Product 1

HCID 118307645HCID 118307645, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.017 g, 0.150 mmol) and triethylamine (0.028 ml, 0.200 mmol) were added to a solution of 5-methyl-N3-[4-(trifluoromethyl)pyrimidin-2-yl]biphenyl-3,3′-diamine (0.034 g, 0.100 mmol) in DCM (1.00 ml) and stirred for 14 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in DMSO (1 mL), then purified by mass triggered reverse phase HPLC to give N-(3′-methyl-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-3-yl)methanesulfonamide. MS ESI calcd. for C19H18F3N4O2S [M+H]+ 423, found 423. 1H NMR (600 MHz, DMSO-d6) δ 10.21 (s, 1H), 8.78 (d, J=4.9 Hz, 1H), 7.83 (s, 1H), 7.52 (s, 1H), 7.40 (dt, J=15.7, 4.8 Hz, 2H), 7.30 (d, J=7.7 Hz, 1H), 7.23 (d, J=4.9 Hz, 1H), 7.17 (dd, J=8.0, 1.3 Hz, 1H), 7.04 (s, 1H), 2.99 (s, 3H), 2.32 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in DMSO (1 mL)
  3. custompurified by mass triggered reverse phase HPLC

Sources & evidence

ORD record
ord-d0dbdcc6f17f4aebb7b53348258efff4
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

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