Methane → HCID 20190410, compound

HRID 1788766Notes

Reaction equation

HRID 1788766 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Cl.Cl[C:18]([C:20]1[CH:21]=[C:22]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[N:23]2[C:27]=1[CH2:26][S:25][CH2:24]2)=[O:19].C>C(Cl)Cl.C(O)CCC>[N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:18]([C:20]2[CH:21]=[C:22]([C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[N:23]3[C:27]=2[CH2:26][S:25][CH2:24]3)=[O:19])[CH:4]=1

Participants

7

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 310183-PyridinemethanamineHCID 20190397HCID 20190397, compound

Product 1

HCID 20190410HCID 20190410, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 3-aminomethylpyridine (5.5 g) and of triethylamine (10.1 g) in methylene chloride (100 cc) is added over 15 minutes at a temperature between 20° and 30° C. to a suspension of 7-chloroformyl-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole hydrochloride (15 g) in methylene chloride (250 cc). The solution obtained is stirred at a temperature of about 20° C. for 16 hours. A product precipitates out. The crystals which have appeared are separated off by filtration, washed 3 times with methylene chloride (300 cc in total) and 3 times with isopropyl ether (200 cc in total) and then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. A crude product (11.3 g) melting at 206° C. is thus obtained. This product is dissolved in boiling 1-butanol (160 cc). The solution obtained is treated with decolourising charcoal (0.5 g) and filtered hot. The filtrate is cooled at a temperature of about 4° C. for 2 hours. The crystals which have appeared are separated off by filtration, washed 4 times with 1-butanol (100 cc in total) and 4 times with diethyl ether (100 cc in total) and are then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets. N-(3-pyridylmethyl)-5-(3-pyridyl)-1H,3H-pyrrolo[1,2-c]thiazole-7-carboxamide (9.9 g) is thus obtained in the form of cream crystals melting at 210° C.

Workup

  1. customThe solution obtained
  2. customA product precipitates out
  3. customThe crystals which have appeared are separated off by filtration
  4. washwashed 3 times with methylene chloride (300 cc in total) and 3 times with isopropyl ether (200 cc in total)
  5. dry with materialdried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets
  6. customA crude product (11.3 g) melting at 206° C. is thus obtained
  7. dissolutionThis product is dissolved
  8. customThe solution obtained
  9. filtrationfiltered hot
  10. temperatureThe filtrate is cooled at a temperature of about 4° C. for 2 hours
  11. customThe crystals which have appeared are separated off by filtration
  12. washwashed 4 times with 1-butanol (100 cc in total) and 4 times with diethyl ether (100 cc in total)
  13. dry with materialare then dried under reduced pressure (20 mm Hg; 2.7 kPa) at a temperature of about 20° C. in the presence of potassium hydroxide pellets

Sources & evidence

ORD record
ord-be1d7015fa194ec1aee8172435d3fa3c
Source dataset
uspto-grants-1987_08
Patent number
US04684658

Reaction notes

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