Hydrochloric Acid → Hydrochloric Acid

HRID 513264Notes

Reaction equation

HRID 513264 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][N:43]([CH3:47])[C:44]([Cl:46])=[O:45]>CN1C(=O)CCC1>[CH3:42][N:43]([CH3:47])[C:44]([N:25]1[CH2:26][CH2:27][CH:22]([C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:8]3[CH:7]=[C:6]([NH:5][CH2:4][C:3]4[CH:28]=[CH:29][CH:30]=[CH:31][C:2]=4[F:1])[C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=3)=[CH:21][CH:20]=2)[CH2:23][CH2:24]1)=[O:45].[ClH:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 81531DiisopropylethylamineHCID 56970645HCID 56970645, compound

Product 2

HCID 313Hydrochloric AcidHCID 56970641HCID 56970641, 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 dimethylcarbamylchloride (0.055 mL, 0.6 mmol). The mixture was stirred at RT for 1 h 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 C27H31FN6O2: 491.5. NMR (CD3OD): 8.12 (1H, s), 7.37 (1H, m), 7.34 (2H, d, J=8.4 Hz), 7.28 (1H, m), 7.17 (1H, m), 7.16-7.10 (3H, m), 5.88 (1H, s), 4.51 (2H, s), 3.82 (2H, m), 2.94 (2H, m), 2.88 (6H, s), 2.80 (1H, m), 1.86 (2H, m), 1.72 (2H, m) ppm.

Workup

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

Sources & evidence

ORD record
ord-cde402ee7fa44bf1ba9715a4ae0d67bc
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

Loading…