Hydrochloric Acid → Hydrochloric Acid

HRID 513263Notes

Reaction equation

HRID 513263 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:7]=1.Cl.CCN(C(C)C)C(C)C.[CH3:42][S:43]([Cl:46])(=[O:45])=[O:44]>CN1C(=O)CCC1>[F:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][NH:5][C:6]1[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=[C:8]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]3[CH2:27][CH2:26][N:25]([S:43]([CH3:42])(=[O:45])=[O:44])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[CH:7]=1.[ClH:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 56970645HCID 56970645, compound

Product 2

HCID 313Hydrochloric AcidHCID 67502794HCID 67502794, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound 4-(2-fluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 106) HCl salt (100 mg, 0.2 mmol) was stirred in 5 mL NMP. To the solution were added DIEA (0.18 mL, 1.0 mmol) and MsCl (0.047 mL, 0.6 mmol). The mixture was stirred at RT for 30 min and quenched with Me2NH. The mixture was concentrated in vacuo and subjected to reverse phase prep HPLC to isolate the title compound as HCl salt. UV=259 nm. M+H found for C25H28FN5O3S: 498.5. NMR (CD3OD): 8.13 (1H, s), 7.39-7.34 (3H, m), 7.29 (1H, td, J=8.0; 2.0 Hz), 7.19-7.10 (4H, m), 5.88 (1H, s), 4.51 (2H, s), 3.86 (2H, m), 2.88 (2H, m), 2.85 (3H, s), 2.75 (1H, m), 1.97 (2H, m), 1.79 (2H, m) ppm.

Workup

  1. customquenched with Me2NH
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fba2d6338dd243e389e691efd279e43d
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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