Acetic Acid → HCID 68716849, compound

HRID 1913202Notes

Reaction equation

HRID 1913202 reaction equation
C(O)(=O)C.N1C=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:11].Cl.[NH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([N:21]2[C:25](=[O:26])[C:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:23][NH:22]2)=[N:19][CH:20]=1.COC1CCC(OC)O1>O>[ClH:11].[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:24]2[C:25](=[O:26])[N:21]([C:18]3[CH:17]=[CH:16][C:15]([CH2:14][N:13]4[CH:9]=[CH:8][CH:7]=[CH:6]4)=[CH:20][N:19]=3)[NH:22][CH:23]=2)[CH:28]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 790982,5-DimethoxytetrahydrofuranHCID 44139914HCID 44139914, compound

Product 1

HCID 68716849HCID 68716849, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

565 mg (9.4 mmol) of acetic acid are initially charged in 0.3 ml of water. 744 mg (9.4 mmol) of pyridine are added slowly. 191 mg (0.6 mmol) of the compound from Example 13 and 74 mg (0.6 mmol) of 2,5-dimethoxytetrahydrofuran are then added, and the mixture is stirred at 100° C. for 16 h. The mixture is then concentrated on a rotary evaporator, 3 ml of acetonitrile and 3 ml of 1 N hydrochloric acid are added and the mixture is stirred at RT for 30 min. The solid formed is filtered off, washed once with water and dried under high vacuum.

Workup

  1. concentrationThe mixture is then concentrated on a rotary evaporator, 3 ml of acetonitrile and 3 ml of 1 N hydrochloric acid
  2. additionare added
  3. stirringthe mixture is stirred at RT for 30 min
  4. customThe solid formed
  5. filtrationis filtered off
  6. washwashed once with water
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-176a0bca19d04dffa05486cc15c17517
Source dataset
uspto-grants-2013_12
Patent number
US08609698B2

Reaction notes

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