Acetone → Hydrochloric Acid

HRID 513262Notes

Reaction equation

HRID 513262 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.[ClH:32].CCN(C(C)C)[CH:36]([CH3:38])[CH3:37].CC(C)=O>ClCCCl.O1CCOCC1.O.CC(O)=O>[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]([CH:36]([CH3:38])[CH3:37])[CH2:24][CH2:23]3)=[CH:20][CH:21]=2)[CH:7]=1.[ClH:32]

Participants

10

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 56970645HCID 56970645, compound

Product 2

HCID 313Hydrochloric AcidHCID 67501679HCID 67501679, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 4-(2-fluorobenzylamino)-6-(4-(piperidin-4-yl)phenylamino)nicotinamide (Example 106) HCl salt (110 mg, 0.24 mmol) was stirred in 5 mL 1,2-dichloroethane (DCE) and 5 mL dioxane. To the slurry were added DIEA (0.21 mL, 1.2 mmol) and acetone (0.18 mL, 2.4 mmol). The mixture was stirred at RT for 1 h. To the mixture were then added HOAc (0.25 mL) and NaBH(OAC)3 (260 mg, 1.2 mmol). The mixture was stirred at RT for overnight. Water (10 mL) was added. The mixture was concentrated in vacuo. The residue was subjected to reverse phase prep HPLC to isolate the title compound as HCl salt. UV=259 nm. M+H found for C27H32FN5O: 462.5. NMR (CD3OD): 8.18 (1H, s), 7.38 (1H, m), 7.30 (2H, d, J=8.8 Hz), 7.09 (3H, m), 7.04 (1H, m), 7.00 (1H, m), 5.82 (1H, s), 4.47 (2H, s), 3.58 (2H, m), 3.22 (3H, m), 2.95 (1H, m), 2.18 (2H, m), 2.01 (2H, m), 1.42 (6H, d, J=6.8 Hz) ppm.

Workup

  1. stirringThe mixture was stirred at RT for overnight
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-725702ebc53f4d67a4a65e9959e6448d
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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