Hydrochloric Acid → HCID 178457930, compound

HRID 2274401Notes

Reaction equation

HRID 2274401 reaction equation
[F:1][C:2]1[C:31]([N:32]2[CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:30][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH:14][C:15](=[O:23])[N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[CH:12][N:11](C4CCCCO4)[N:10]=3)=[N:8][C:4]=2[CH:3]=1.Cl>O1CCOCC1>[F:1][C:2]1[C:31]([N:32]2[CH2:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)=[CH:30][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH:14][C:15](=[O:23])[N:16]([CH:17]([CH3:18])[CH3:19])[CH:20]([CH3:22])[CH3:21])=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178457925HCID 178457925, compound

Product 1

HCID 178457930HCID 178457930, compoundYield 9.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 600 mg of 3-[3-(5-fluoro-6-perhydro-1,4-oxazepin-4-yl-1H-benzimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1,1-diisopropylurea in solution in 5 mL of a 4N solution of hydrochloric acid in dioxane is stirred at 22° C. for 4 hours. After evaporation, the reaction crude is purified by preparative HPLC and then by preparative LC/MS, with, as eluent, a gradient of water, with acetonitrile, containing respectively 0.07% of trifluoroacetic acid. 48 mg of 3-[3-(5-fluoro-6-perhydro-1,4-oxazepin-4-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-1,1-diisopropylurea are obtained in the form of a brown solid. 1H NMR (400 MHz, DMSO-d6, δ in ppm): 1.35 (d, J=7.0 Hz, 12H); 1.98 (m, 2H); 3.33 (m, 4H); 3.78 (m, 4H); 4.06 (m, 2H); 7.08 (broad d J=8.0 Hz, 1H); 7.28 (broad d, J=12.0 Hz, 1H); 8.01 (s, 1H); 9.56 (s, 1H); 12.85 (broad m, 2H).

Workup

  1. customAfter evaporation
  2. customthe reaction crude
  3. customis purified by preparative HPLC
  4. additionby preparative LC/MS, with, as eluent, a gradient of water, with acetonitrile, containing respectively 0.07% of trifluoroacetic acid

Sources & evidence

ORD record
ord-4dde92af8aab441ab98db2c00395f82d
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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