Isopropanol hydrochloride → HCID 24765038, compound

HRID 1666767Notes

Reaction equation

HRID 1666767 reaction equation
[P:1]([O:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[CH2:33][NH:34][C:35]([NH:37][C:38]3[N:42]([C:43]4[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=4)[N:41]=[C:40]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:39]=3)=[O:36])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].Cl.CC(O)C>CCO>[P:1]([O:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=3[CH2:33][NH:34][C:35]([NH:37][C:38]3[N:42]([C:43]4[CH:44]=[CH:45][C:46]([CH3:49])=[CH:47][CH:48]=4)[N:41]=[C:40]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH:39]=3)=[O:36])=[CH:22][CH:23]=2)[CH:18]=[N:17]1)([OH:8])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 21912024Isopropanol hydrochlorideHCID 57552289HCID 57552289, compound

Product 1

HCID 24765038HCID 24765038, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of di-tert-butyl 2-(5-(2-((3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)methyl)-4-fluorophenoxy)-1H-indazol-1-yl)ethyl phosphate (3.66 g, 4.89 mmol) in EtOH (0.2M, 24 mL) was treated with SN HCl/iPrOH (2.93 mL, 14.7 mmol) at room temperature. Stirring at room temperature was continued overnight. The solvent was evaporated in vacuo, and the residue was coevaporated from toluene, and ether (2×). The beige foam was taken in MeOH and poured slowly into a beaker containing water. The precipitated solids were collected by filtration to provide 2.83 g (91%) of the desired product. MS (APCI+) m/z 637 (M+1) was detected. 1H NMR (400 MHz, DMSO-d6) δ 8.30 (s, 1H), 8.00 (s, 1H), 7.71 (d, 1H, J=9 Hz), 6.88-7.37 (m, 10H), 6.24 (s, 1H), 4.61 (br, 1H), 4.28 (d, 2H, J=5.7 Hz), 4.19 (dd, 2H, J=5.2 Hz), 2.35 (s, 3H), 1.25 (s, 9H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionpoured slowly into a beaker
  3. additioncontaining water
  4. filtrationThe precipitated solids were collected by filtration

Sources & evidence

ORD record
ord-399a9f0b0b634a5fb824c5baade2e2ce
Source dataset
uspto-grants-2011_10
Patent number
US08044083B2

Reaction notes

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