Water → HCID 86745285, compound

HRID 1460530Notes

Reaction equation

HRID 1460530 reaction equation
Cl.Cl[CH2:3][CH2:4][C:5]1[C:10](=[O:11])[N:9]2[CH2:12][CH2:13][CH2:14][CH2:15][C:8]2=[N:7][C:6]=1[CH3:16].Br.Br.[NH:19]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[N:29]([CH2:30][C:31]3[N:32]=[CH:33][S:34][CH:35]=3)[C:28]3[CH:36]=[CH:37][CH:38]=[CH:39][C:27]=3[N:26]=2)[CH2:20]1.[C:40](=[O:43])([O-:42])[O-].[Na+].[Na+].[I-].[K+].[OH2:48]>CN(C)C(=O)C>[C:10]([OH:11])(=[O:48])/[CH:5]=[CH:6]/[C:40]([OH:42])=[O:43].[CH3:16][C:6]1[N:7]=[C:8]2[CH2:15][CH2:14][CH2:13][CH2:12][N:9]2[C:10](=[O:11])[C:5]=1[CH2:4][CH2:3][N:19]1[CH2:23][CH2:22][CH:21]([NH:24][C:25]2[N:29]([CH2:30][C:31]3[N:32]=[CH:33][S:34][CH:35]=3)[C:28]3[CH:36]=[CH:37][CH:38]=[CH:39][C:27]=3[N:26]=2)[CH2:20]1

Participants

7

Reactant 5

HCID 962WaterHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 156057823-(2-Chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one--hydrogen chloride (1/1)HCID 19875944HCID 19875944, compound

Product 1

HCID 86745285HCID 86745285, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4.2 parts of 3-(2-chloroethyl)-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one monohydrochloride, 6.9 parts of N-(3-pyrrolidinyl)-1-(4-thiazolylmethyl)-1H-benzimidazol-2-amine dihydrobromide, 9.7 parts of sodium carbonate, 0.1 parts of potassium iodide and 90 parts of N,N-dimethylacetamide was stirred for 1.5 hour at 100° C. After cooling, the reaction mixture was poured into 500 parts of water. The product was extracted three times with dichloromethane. The combined extracts were washed with water, dried, filtered and evaporated. The oily residue was converted into the (E)-2-butenedioate salt in 180 parts of 2-propanone and ethanol. The salt was filtered off and dried, yielding 6 parts (51.2%) of 6,7,8,9-tetrahydro-2-methyl-3-[2-[3-[[1-(4-thiazolylmethyl)-1H-benzimidazol-2-yl]amino]-1-pyrrolidinyl]ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one (E)-2-butenedioate (2:5); mp. 148.1° C. (compound 59).

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted three times with dichloromethane
  3. washThe combined extracts were washed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. customdried

Sources & evidence

ORD record
ord-2f5e06c402f34e518e7e1ce14497374f
Source dataset
uspto-grants-1991_12
Patent number
US05071846

Reaction notes

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