Methylamine → HCID 59725904, compound

HRID 1912881Notes

Reaction equation

HRID 1912881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:29])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:25]=[N:24][C:23]4[C:18]3=[N:19][CH:20]=[N:21][C:22]=4[C:26](O)=[O:27])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:30]([F:33])([F:32])[F:31].CN.[CH3:36][N:37](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=NC2N(O)N=NC=2C=1>CN(C)C=O>[CH3:36][NH:37][C:26]([C:22]1[N:21]=[CH:20][N:19]=[C:18]2[C:23]=1[N:24]=[CH:25][N:17]2[C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:30]([F:32])([F:31])[F:33])[CH:4]=2)=[O:29])=[CH:16][CH:15]=1)=[O:27]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23154947HCID 23154947, compound

Product 1

HCID 59725904HCID 59725904, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 3 mL of dimethylformamide, 30 mg (0.063 mmol) of 9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purine-6-carboxylic acid was dissolved, and 10 μL of 40% methylamine, 17 mg (0.13 mmol) of HATU and HOAt (0.13 mmol) were added thereto and the mixture solution was stirred at room temperature overnight. The reaction solution was partitioned between ethyl acetate and water and the organic layer was washed with water and a saturated sodium chloride solution in the order named, and then concentrated under reduced pressure. The coarse product was recrystallized from ethyl acetate to obtain 16 mg (52%) of a target product as a white solid.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe coarse product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7e66bf7476684d5eb9ac7d56ca279158
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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