Tris(hydroxymethyl)aminomethane → HCID 10154873, compound

HRID 1348933Notes

Reaction equation

HRID 1348933 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][C:10]3[C:14]([C:15]([O:17]CC)=O)=[N:13][N:12]([C:20]4[CH:28]=[CH:27][C:23]5[O:24][CH2:25][O:26][C:22]=5[CH:21]=4)[C:11]=3[C:4]=2[CH:3]=1.ClC1[N:38]=CC=CC=1C(Cl)=O.C(O)C(N)(CO)CO>N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][C:10]3[C:14]([C:15]([NH2:38])=[O:17])=[N:13][N:12]([C:20]4[CH:28]=[CH:27][C:23]5[O:24][CH2:25][O:26][C:22]=5[CH:21]=4)[C:11]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 27745412-Chloronicotinoyl chlorideHCID 21092647HCID 21092647, compound

Product 1

HCID 10154873HCID 10154873, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of title material from Example 28 (0.0791 g, 0.226 mmol) in dry pyridine (3 ml), 2-chloronicotinoyl chloride (0.0487 g, 0.2712 mmol) was added. The reaction was stirred at RT overnight. The reaction was quenched with PS-trisamine (4.61 mmol/g, 0.2021 g, 0.9318 mmol) and stirred overnight. The resins were filtrated, washed with pyridine. The combined filtrate and washes were concentrated to dryness. The resulting residue was recrystallized with hot methanol, to give 8-amino-1-[1,3-benzodioxol-5-yl]-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide (0.0922 g, 83.3%), which was characterized by 1H NMR, LC/MS (MH+ 489), and HPLC (96.6% purity).

Workup

  1. stirringstirred overnight
  2. filtrationThe resins were filtrated
  3. washwashed with pyridine
  4. concentrationThe combined filtrate and washes were concentrated to dryness
  5. customThe resulting residue was recrystallized with hot methanol

Sources & evidence

ORD record
ord-ea203bdf38e442038c7e4c5555b4c602
Source dataset
uspto-grants-2007_05
Patent number
US07211597B2

Reaction notes

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