Hydrochloric Acid → HCID 23028131, compound

HRID 1946464Notes

Reaction equation

HRID 1946464 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([S:14]([NH2:17])(=[O:16])=[O:15])=[C:11]([CH3:13])[N:12]=2)[CH:9]=1)[CH3:2].[CH3:18][O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([NH:28][C:29](=O)[O:30]C2C=CC=CC=2)[N:21]=1.C1CCN2C(=NCCC2)CC1.Cl>C(#N)C.O>[CH3:27][O:26][C:24]1[CH:25]=[C:20]([O:19][CH3:18])[N:21]=[C:22]([NH:28][C:29]([NH:17][S:14]([C:10]2[N:8]3[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=[CH:6][C:7]3=[N:12][C:11]=2[CH3:13])(=[O:15])=[O:16])=[O:30])[N:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10945667Carbamic acid, N-(4,6-dimethoxy-2-pyrimidinyl)-, phenyl esterHCID 23028146HCID 23028146, compound

Product 1

HCID 23028131HCID 23028131, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

As shown in the above reaction scheme, 6-ethoxy-2-methylimidazo[1,2-a]pyridin-3-sulfonamide (0.04 g, 0.156 mmol) and phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate (0.048 g, 0.172 mmol) were suspended in acetonitrile (1 ml) and stirred at room temperature, during which DBU (0.026 g, 0.172 mmol) was added thereto. After the mixture was stirred at room temperature for 2 hours, the reaction solution was poured into water (20 ml) and adjusted to pH 3 with dilute hydrochloric acid. The precipitated crystals were collected by filtration, and washed with water and ether in this order. The crystals were dried under reduced pressure to give the title compound as pale brown crystals. The yield was 0.06 g (87%), and the melting point was 159 to 164° C. (dec.).

Workup

  1. additionwas added
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water and ether in this order
  4. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-18ef868406a74ffaacdaa9806e5363b4
Source dataset
uspto-grants-2013_03
Patent number
US08399381B2

Reaction notes

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