Acetic Anhydride → HCID 58529566, compound

HRID 1972827Notes

Reaction equation

HRID 1972827 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[O:32][CH2:31][CH:30]5[CH2:33][NH:34][CH2:35][CH2:36][N:29]5[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:44](OC(=O)C)(=[O:46])[CH3:45]>CN(C=O)C>[C:44]([N:34]1[CH2:35][CH2:36][N:29]2[CH:30]([CH2:31][O:32][CH:27]([C:19]3[N:20]4[C:25]([C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)=[C:17]([C:12]4[CH:13]=[CH:14][C:15]5[C:10]([CH:11]=4)=[N:9][N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:16]=5)[CH:18]=3)[CH2:28]2)[CH2:33]1)(=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 58529380HCID 58529380, compound

Product 1

HCID 58529566HCID 58529566, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(2-benzyl-2H-indazol-6-yl)-7-(octahydropyrazino[2,1-c][1,4]oxazin-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (50 mg, 0.10 mmol), triethylamine (29 μL, 0.21 mmol), in DMF (1 mL) at 0° C., acetic anhydride (11 μL, 0.11 mmol) was added. The reaction was allowed to stir for 20 minutes while warming to rt. The mixture was partitioned between ethyl acetate (30 mL) and saturated aqueous K2CO3 solution (10 mL). The layers were separated and the organic phase was washed, dried (Na2SO4), and concentrated to dryness. The residue was triturated with Et2O to obtain 19 mg (35%) of the desired product. 1H-NMR (DMSO-d6) 8.53 (s, 1H), 7.91 (s, 1H), 7.78 (d, 1H), 7.57 (s, 1H), 7.35-7.28 (m, 5H), 7.10 (dd, 1H), 6.71 (s, 1H), 5.64 (s, 2H), 5.14 (dd, 1 H), 4.33-4.21 (m, 1H), 3.91-3.84 (m, 1H), 3.79-3.68 (m, 1H), 3.39-3.27 (m, 2H), 3.06-3.00 (m, 1H), 2.76-2.64 (m, 2H), 2.41-2.37 (m, 1H), 223-2.11 (m, 1H), 2.07-1.95 (m, 1H), 1.99 (s, 3H); LC-MS [M+H]+=523, RT=2.24 min.

Workup

  1. customThe mixture was partitioned between ethyl acetate (30 mL) and saturated aqueous K2CO3 solution (10 mL)
  2. customThe layers were separated
  3. washthe organic phase was washed
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-9cd98a62aa754c9d9ccc2066ccacacb1
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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