Hydrochloric Acid → HCID 66590088, compound

HRID 1166292Notes

Reaction equation

HRID 1166292 reaction equation
Cl.C(O[C:7](=O)[N:8]([CH:10]1[CH2:15][CH2:14][CH:13]([N:16]([C:34]([C:36]2[S:40][C:39]3[CH:41]=[CH:42][CH:43]=[CH:44][C:38]=3[C:37]=2[Cl:45])=[O:35])[CH2:17][C:18]2[CH:19]=[C:20]([C:26]3[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=3)[C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:12][CH2:11]1)C)(C)(C)C.C(O)C>C(OC)(C)(C)C>[ClH:45].[C:32]([C:29]1[CH:30]=[CH:31][C:26]([C:20]2[C:21]([O:24][CH3:25])=[CH:22][CH:23]=[C:18]([CH2:17][N:16]([CH:13]3[CH2:12][CH2:11][CH:10]([NH:8][CH3:7])[CH2:15][CH2:14]3)[C:34]([C:36]3[S:40][C:39]4[CH:41]=[CH:42][CH:43]=[CH:44][C:38]=4[C:37]=3[Cl:45])=[O:35])[CH:19]=2)=[CH:27][CH:28]=1)#[N:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66589936HCID 66589936, compound

Product 1

HCID 66590088HCID 66590088, compoundYield 201.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Concentrated hydrochloric acid (27.5 mL) was added to a solution of compound 6 (11.0 g, 17.1 mmol) and ethanol (82.5 mL). The mixture was stirred until reaction was complete as monitored by TLC. The mixture was concentrated in vacuo and dichloromethane added and concentrated again, this was repeated until a solid was obtained. The solid was then slurried with t-butylmethyl ether (30 mL), filtered, and the organic layer dried (MgSO4) and concentrated in vacuo to give the title compound 7 (10.0 g, 99%): δH (360 MHz: DMSO, 70° C.) 1.30-1.50 (m, 2H), 1.85 (br s, 4H), 2.12 (br d, 2H), 2.48 (s, 3H), 2.91 (br t, 1H), 3.81 (s, 3H), 3.87 (br s, 1H), 4.71 (s, 2H), 7.14 (d, 1H), 7.29 (s, 1H), 7.40 (d, 1H), 7.57-7.68 (m, 4H), 7.80-7.90 (m, 3H), 8.09 (d, 1H), 8.82 (br s, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo and dichloromethane
  2. additionadded
  3. concentrationconcentrated again
  4. customwas obtained
  5. filtrationfiltered
  6. dry with materialthe organic layer dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbff54349866429095ff0cf71ca42b27
Source dataset
uspto-grants-2003_09
Patent number
US06613798B1

Reaction notes

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