Hydrochloric Acid → HCID 178495917, compound

HRID 1508144Notes

Reaction equation

HRID 1508144 reaction equation
[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([NH:17][CH2:18][CH2:19][O:20][CH3:21])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1.[ClH:33]>C(O)(C)C>[ClH:33].[CH3:1][C:2]1([CH3:32])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([NH:17][CH2:18][CH2:19][O:20][CH3:21])([CH3:15])[CH3:16])[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178495916HCID 178495916, compound

Product 1

HCID 178495917HCID 178495917, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-cyano-1H-imidazole-2-carboxylic acid {2-(4,4-dimethyl-cyclohex-1-enyl)-4-[1-(2-methoxy-ethylamino)-1-methyl-ethyl]-phenyl}-amide (750 mg, 1.72 mmol, as prepared in Example 20) in isopropanol (dissolved with heating) was treated with HCl (331 μL, 1.72 mmol, 5.2 M in isopropanol) at RT for 1 h. The resulting precipitate was filtered, washed with cold hexanes, and dried under high vacuum to afford the title compound (438 mg, 54%) as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.40 (d, 1H, J=9.2 Hz), 8.04 (s, 1H), 7.50 (dd, 1H, J=9.2, 2.8 Hz), 7.43 (d, 1H, J=2.8 Hz), 5.86-5.80 (m, 1H), 3.59-3.52 (m, 2H), 3.38 (s, 3H), 2.97-2.89 (m, 2H), 2.40-2.32 (m, 2H), 2.16-2.10 (m, 2H), 1.82 (s, 6H), 1.68-1.60 (m, 2H), 1.13 (s, 6H). Mass spectrum (APCI, m/z): Calcd. for C25H33N5O2, 436.3 (M+H). found 435.8.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with cold hexanes
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-c380764169ae4ebf9cd884648a943b91
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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