Water → HCID 11453060, compound

HRID 2054418Notes

Reaction equation

HRID 2054418 reaction equation
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].C(N(C(C)C)CC)(C)C.Cl[C:16]1[N:21]2[N:22]=[C:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[C:24]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[C:20]2[N:19]=[C:18]([CH3:39])[N:17]=1.O>CN(C=O)C>[CH2:1]([NH:5][C:16]1[N:21]2[N:22]=[C:23]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])[C:24]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[C:20]2[N:19]=[C:18]([CH3:39])[N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8007ButylamineHCID 81531DiisopropylethylamineHCID 59655729HCID 59655729, compound

Product 1

HCID 11453060HCID 11453060, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of butylamine (0.17 ml, 0.15 mmol) and diisopropylethylamine (0.037 ml, 0.21 mmol) in DMF (0.75 ml) was added a solution of 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 54 mg, 0.14 mmol) in DMF (1.3 ml). After stirring for 40 hours, the reaction was treated with water, dropwise, until a precipitate formed. After several more hours of stirring, the resultant solid was collected by vacuum filtration, and then washed with water and a small amount of isopropyl alcohol to afford 7A-1 (46 mg, 77%) as a solid: +APcI MS (M+1) 426.2; 1H NMR (400 MHz, CD3OD) δ 7.51-7.30 (m, 6H), 7.22-7.18 (m, 2H), 3.63 (t, J=7.1 Hz, 2H), 2.50 (s, 3H), 1.70 (quintet, J=7.3 Hz, 2H), 1.44 (hextuplet, J=7.5 Hz, 2H), 0.98 (t, J=7.5 Hz, 2H).

Workup

  1. customdropwise, until a precipitate formed
  2. stirringAfter several more hours of stirring
  3. filtrationthe resultant solid was collected by vacuum filtration
  4. washwashed with water
  5. customa small amount of isopropyl alcohol to afford 7A-1 (46 mg, 77%) as a solid

Sources & evidence

ORD record
ord-65b206a65dcc4009acc759ebc09a0c10
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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