Hydrochloric Acid → HCID 59599446, compound

HRID 1627565Notes

Reaction equation

HRID 1627565 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][C:14]3([OH:27])[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)[CH:12]=2)=[CH:4][C:3]=1[O:28][CH:29]([C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=1[Cl:39])[CH3:30].Cl.O1CCOCC1>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH2:13][C:14]3([OH:27])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:12]=2)=[CH:4][C:3]=1[O:28][CH:29]([C:31]1[C:36]([Cl:37])=[CH:35][CH:34]=[C:33]([F:38])[C:32]=1[Cl:39])[CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59599417HCID 59599417, compound

Product 1

HCID 59599446HCID 59599446, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction mixture of compound (3-6) (145 mg; 0.25 mmol) with 4.0 M HCl in dioxane (2.0 mL; 8.1 mmol) in 5 mL of CH2Cl2 was stirred at room temperature for 2.0 hours. The reaction mixture was concentrated by vacuum. The residue was purified by Dionex system (5% to 95% MeCN:H2O w 0.1% HOAc buffer) to collect the desired fraction to afford 76 mg of (3-7) as a yellow grease (63% yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.41-1.55 (m, 2H) 1.59-1.71 (m, 2H) 1.81 (d, J=6.57 Hz, 3H) 2.88-3.00 (m, 2H) 3.02-3.14 (m, 2H) 4.08 (s, 2H) 5.17 (s, 2H) 6.14-6.27 (m, J=6.57 Hz, 1H) 7.05 (s, 1H) 7.40-7.49 (m, J=8.72, 8.72 Hz, 1H) 7.51-7.60 (m, J=9.09, 4.80 Hz, 1H) 7.63 (s, 1H) 7.76 (s, 1H) 7.91 (s, 1H) 8.51 (s, 1H) 8.81 (s, 1H). LCMS calcd for C22H24Cl2FN5O2 (M+H) 481, found 481. HPLC purity 98%. Anal. (C22H24Cl2FN5O2×2.2HOAc×2.3H2O)C, H, N.

Workup

  1. concentrationThe reaction mixture was concentrated by vacuum
  2. customThe residue was purified by Dionex system (5% to 95% MeCN:H2O w 0.1% HOAc buffer)
  3. customto collect the desired fraction

Sources & evidence

ORD record
ord-ae2524c6ef43473dba4d7bec0a1f0c5a
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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