2-Pyrazinecarboxylic acid → HCID 45110639, compound

HRID 238069Notes

Reaction equation

HRID 238069 reaction equation
Cl.[NH2:2][C@@H:3]1[C:17](=[O:18])[N:16]2[CH2:19][C@H:20]([O:22][C:23]3[N:24]=[C:25]4[C:30](=[C:31]5[C:36]=3[CH:35]=[CH:34][CH:33]=[CH:32]5)[CH:29]=[CH:28][CH:27]=[CH:26]4)[CH2:21][C@H:15]2[C:14](=[O:37])[NH:13][C@:12]2([C:39]([NH:41][S:42]([CH:45]3[CH2:47][CH2:46]3)(=[O:44])=[O:43])=[O:40])[CH2:38][C@H:11]2[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[N:48]1[CH:53]=[CH:52][N:51]=[CH:50][C:49]=1[C:54](O)=[O:55].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH:45]1([S:42]([NH:41][C:39]([C@@:12]23[CH2:38][C@H:11]2[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]([NH:2][C:54]([C:49]2[CH:50]=[N:51][CH:52]=[CH:53][N:48]=2)=[O:55])[C:17](=[O:18])[N:16]2[CH2:19][C@H:20]([O:22][C:23]4[N:24]=[C:25]5[C:30](=[C:31]6[C:36]=4[CH:35]=[CH:34][CH:33]=[CH:32]6)[CH:29]=[CH:28][CH:27]=[CH:26]5)[CH2:21][C@H:15]2[C:14](=[O:37])[NH:13]3)=[O:40])(=[O:43])=[O:44])[CH2:46][CH2:47]1

Participants

6

Reactant 4

HCID 10472-Pyrazinecarboxylic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68499875HCID 68499875, compound

Product 1

HCID 45110639HCID 45110639, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of Example 25a (320 mg, 0.47 mmol) in dimethylformamide (5 mL) was added pyrazinecarboxylic acid (0.065 g, 0.52 mmol), HATU (214 mg, 0.56 mmol) and diisopropylethylamine (0.2 mL, 1.18 mmol). The reaction mixture was stirred at 25° C. for 2 h and then partitioned between 5% aqueous sodium bicarbonate and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was purified by crystallization from ethyl acetate/hexane to give the desired product (155 mg, 44% yield) as an off-white solid.

Workup

  1. custompartitioned between 5% aqueous sodium bicarbonate and ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by crystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-46539cf9a7ac4a3da3b0de4cdf7bfe4b
Source dataset
uspto-grants-2014_02
Patent number
US08642538B2

Reaction notes

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