Hydrochloric Acid → HCID 178457929, compound

HRID 2274442Notes

Reaction equation

HRID 2274442 reaction equation
[F:1][C:2]1[C:31]([N:32]2[CH2:38][CH2:37][CH2:36][N:35]([CH3:39])[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][N:35]([CH3:39])[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 178457924HCID 178457924, compound

Product 1

HCID 178457929HCID 178457929, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 278.5 mg of 3-[3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1,1-diisopropylurea in solution in 5.1 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 with, as eluent, a gradient of water/acetonitrile containing respectively 0.07% of trifluoroacetic acid. 15.2 mg of 3-{3-[5-fluoro-6-(4-methylperhydro-1,4-diazepin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}-1,1-diisopropylurea are isolated in the form of a trifluoroacetate salt. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.26 (d, J=7.0 Hz, 12H); 2.21 (broad m, 2H); 2.90 (s, 3H); from 3.14 to 3.68 (m, 8H); 3.90 (m, 2H); 7.16 (d, J=8.0 Hz, 1H); 7.48 (d, J=12.0 Hz, 1H); 7.98 (s, 1H). ES mass spectrum: m/z=457: MH+(base peak)—m/z=330 (MH−C7H13NO)+.

Workup

  1. customAfter evaporation
  2. customthe reaction crude
  3. customis purified by preparative HPLC with, as eluent

Sources & evidence

ORD record
ord-792cea7ec4b043f29806d57d0308d28a
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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