Diisopropylethylamine → HCID 178424382, compound

HRID 1017981Notes

Reaction equation

HRID 1017981 reaction equation
C[O:2][C:3](=[S:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][N:6]=1.[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:33])[NH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH:11][C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:2])=[S:12])=[N:6][CH:7]=2)=[O:31])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 66052544-((((2-Methylphenyl)amino)carbonyl)amino)benzeneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18404651HCID 18404651, compound

Product 1

HCID 178424382HCID 178424382, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-(pyrid-2-yl)-thioacetic acid methyl ester [930 mg, Reference Example 1(a)], 4-[3-(2-methylphenyl)ureido]phenylacetic acid (1.26 g, prepared as described in Example 21 of International Patent Application Publication No. WO 96/22966), O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (1.69 g) and diisopropylethylamine (1.2 g) in dimethylformamide (50 ml) was stirred at ambient temperature for 1 hour. The mixture was evaporated then poured into water (500 ml). The resultant solid was washed with water (50 ml) and then washed twice with diethyl ether (50 ml). The solid was suspended in methanol (100 ml), then treated with sodium hydroxide solution (10 ml, 1M). The mixture was heated at reflux for 5 hours, then cooled, then evaporated. The residue was treated with hydrochloric acid (200 ml, 1M). The resultant solid was filtered, washed with water (20 ml), then washed twice with diethyl ether (20 ml), then recrystallised from ethanol to give the title compound (220 mg) as a yellow solid, m.p. >235° C. (with decomposition). MS: MH+ 451.

Workup

  1. customprepared
  2. customThe mixture was evaporated
  3. additionthen poured into water (500 ml)
  4. washThe resultant solid was washed with water (50 ml)
  5. washwashed twice with diethyl ether (50 ml)
  6. additiontreated with sodium hydroxide solution (10 ml, 1M)
  7. temperatureThe mixture was heated
  8. temperatureat reflux for 5 hours
  9. temperaturecooled
  10. customevaporated
  11. additionThe residue was treated with hydrochloric acid (200 ml, 1M)
  12. filtrationThe resultant solid was filtered
  13. washwashed with water (20 ml)
  14. washwashed twice with diethyl ether (20 ml)
  15. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-2a7232f88efd403fa20b4f00d081bb9d
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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