Ammonia → HCID 137241982, compound

HRID 966152Notes

Reaction equation

HRID 966152 reaction equation
C(C1C(C(C)C)=[C:6]2N(C=1)N=[CH:9][N:8]=[C:7]2[NH:13]C1C=CC(C)=C(C=1)C(NOC)=O)(=O)C.Cl.CN(C)[CH2:32][CH2:33][CH2:34]N=C=NCC.C1C=CC2N([OH:50])N=NC=2C=1.C([N:53]([CH2:56][CH3:57])[CH2:54][CH3:55])C.N.C[N:60](C)[CH:61]=[O:62]>>[CH3:6][C:7]1[NH:8][C:9](=[O:50])[C:56]2=[C:57]([CH:33]([CH3:32])[CH3:34])[C:55]([C:61]([NH2:60])=[O:62])=[CH:54][N:53]2[N:13]=1

Participants

7

Reactant 6

HCID 222AmmoniaHCID 6228DimethylformamideHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22313104HCID 22313104, compound

Product 1

HCID 137241982HCID 137241982, compoundYield 59%

Procedure

To a solution of compound A of Example 28 (663 mg, 3 mmol) in dimethyl formamide (10 mL) were added were added successively 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (670 mg, 3.5 mmol), HOBt (460 mg, 3 mmol), and triethylamine (0.5 mL, 3.5 mmol). After 2 h, aqueous ammonia (1 mL, 6N) was added. After 1 h, the mixture was concentrated and the residue was partitioned between ethyl acetate (30 mL) and aqueous NaHCO3 (15 mL). The organic layer was separated, dried, and concentrated to afford methyl-5-(1-methylethyl)pyrrolo[2,1-f][1,2,4]triazin-4(3H)-one-6-carboxamide (390 mg, 59%) as white solid. LC/MS; (M+H)+=221.1.

Workup

  1. waitAfter 1 h
  2. concentrationthe mixture was concentrated
  3. customthe residue was partitioned between ethyl acetate (30 mL) and aqueous NaHCO3 (15 mL)
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c347164ab454659a86c20a2802d5c3b
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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