HCID 178457927, compound → HCID 178457932, compound

HRID 2274422Notes

Reaction equation

HRID 2274422 reaction equation
[F:1][C:2]1[C:31]([N:32]2[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>[F:1][C:2]1[C:31]([N:32]2[CH2:33][CH2:34][O:35][CH2:36][CH2:37]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]([CH3:18])[CH3:19])=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 178457927HCID 178457927, compound

Product 1

HCID 178457932HCID 178457932, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 550 mg of 3-[3-(5-fluoro-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1,1-diisopropylurea in 8.5 mL of concentrated hydrochloric acid is stirred at ambient temperature for 12 hours and the medium is concentrated under vacuum in a rotary evaporator. The reaction crude is purified by preparative LC/MS, elution being carried out with a mixture of water and acetonitrile containing respectively 0.07% of trifluoroacetic acid. 183 mg of 3-[3-(5-fluoro-6-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-1,1-diisopropylurea in the form of a trifluoroacetate salt are isolated. 1H NMR (400 MHz, DMSO-d6, δ in ppm): 1.35 (d, J=7.0 Hz, 12H); 3.00 (m, 4H); 3.78 (m, 4H); 4.07 (m, 2H); 7.08 (broad d, J=7.5 Hz, 1H); 7.32 (broad d, J=12.0 Hz, 1H); 8.03 (s, 1H); 9.57 (s, 1H); 12.95 (broad m, 2H).

Workup

  1. concentrationthe medium is concentrated under vacuum in a rotary evaporator
  2. customThe reaction crude
  3. customis purified by preparative LC/MS, elution
  4. additionbeing carried out with a mixture of water and acetonitrile containing respectively 0.07% of trifluoroacetic acid

Sources & evidence

ORD record
ord-fb3b8cb60fbf430696b1dfc91c624c6c
Source dataset
uspto-grants-2015_09
Patent number
US09126969B2

Reaction notes

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