Hydrochloric Acid → HCID 71737480, compound

HRID 715140Notes

Reaction equation

HRID 715140 reaction equation
Cl.[CH:2]1([NH:9][C:10](=[O:39])[NH:11][C:12]2[C:13]([F:38])=[CH:14][C:15]([CH3:37])=[C:16]([C:18]3[C:19]([CH3:36])=[N:20][C:21]4[C:26]([CH:27]=3)=[CH:25][N:24]=[C:23]([NH:28]C(=O)OC(C)(C)C)[CH:22]=4)[CH:17]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>CO>[NH2:28][C:23]1[CH:22]=[C:21]2[C:26]([CH:27]=[C:18]([C:16]3[C:15]([CH3:37])=[CH:14][C:13]([F:38])=[C:12]([NH:11][C:10]([NH:9][CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]4)=[O:39])[CH:17]=3)[C:19]([CH3:36])=[N:20]2)=[CH:25][N:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89827767HCID 89827767, compound

Product 1

HCID 71737480HCID 71737480, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Add HCl (6.0 M, 1.058 mL, 6.35 mmol) to a solution of tert-butyl (3-(5-(3-cycloheptylureido)-4-fluoro-2-methylphenyl)-2-methyl-1,6-naphthyridin-7-yl)carbamate (0.331 g, 0.635 mmol) in MeOH (10 mL) and heat at 50° C. for 1 h. Cool to RT, concentrate to dryness, add DCM and TEA and concentrate to dryness again. Add water to the residue, extract with DCM (4×), dry the combined organics over Na2SO4, concentrate to dryness and purify via silica gel chromatography (MeOH/DCM) to afford the title compound (202 mg, 76%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.82 (s, 1H), 8.21 (s, 1H), 7.95 (m, 2H), 7.16 (d, J=12.3 Hz, 1H), 6.65-6.62 (m, 2H), 6.39 (s, 2H), 3.62 (s, 1H), 2.28 (s, 3H), 1.95 (s, 3H), 1.76 (m, 2H), 1.44-1.41 (m, 10H); MS (ESI) m/z: 422.2 (M+H+).

Workup

  1. temperatureCool to RT
  2. concentrationconcentrate to dryness
  3. additionadd DCM and TEA
  4. concentrationconcentrate to dryness again
  5. extractionAdd water to the residue, extract with DCM (4×)
  6. dry with materialdry the combined organics over Na2SO4
  7. concentrationconcentrate to dryness
  8. custompurify via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record
ord-5cb2335128994085bd1a6750ff3d22e7
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…