Dimethylformamide → HCID 68322710, compound

HRID 1521753Notes

Reaction equation

HRID 1521753 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][C:19](C(O)=O)=[CH:20][C:15]=2[NH:14][CH:13]1[C:24]([O:29][CH3:30])([O:27][CH3:28])[O:25][CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](O[N:48]2N=[N:55][C:50]3[CH:51]=[CH:52][CH:53]=C[C:49]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.NC1C=NC=CC=1.C(N(CC)CC)C.CN([CH:81]=[O:82])C>CCOC(C)=O>[N:48]1[CH:53]=[CH:52][CH:51]=[C:50]([NH:55][C:81]([C:18]2[CH:19]=[CH:20][C:15]3[N:14]=[C:13]([C:24]([O:27][CH3:28])([O:25][CH3:26])[O:29][CH3:30])[N:12]([CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:16]=3[CH:17]=2)=[O:82])[CH:49]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 100093-AminopyridineHCID 2724699PyBOPHCID 89585648HCID 89585648, compound2×

Product 1

HCID 68322710HCID 68322710, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 1-(3-tert-butoxycarbonylamino-propyl)-2-trimethoxymethyl-3H-benzimidazole-5-carboxylic acid (Intermediate A, 70 mg, 0.17 mmol) and PyBOP (95 mg, 0.18 mmol) in DMF (1 mL) was stirred for 10 min, and 3-aminopyridine (17 mg, 0.18 mmol) and triethylamine (46 μL, 0.33 mmol) are added. The solution is heated in a block heater at 45° C. for 20 h. The solution is diluted with EtOAc and is washed with Na2CO3, H2O, and brine. The organic layer is dried (MgSO4) and evaporated to afford the title compound (102 mg, 0.16 mmol, 99%) as an oil that was used in the next step without purification.

Workup

  1. washis washed with Na2CO3, H2O, and brine
  2. dry with materialThe organic layer is dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-210ba6f0c9e04dc9a49f572c52ac5cdc
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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