1-Hydroxybenzotriazole → HCID 69512524, compound

HRID 1272727Notes

Reaction equation

HRID 1272727 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1([NH:28][C:29]([C:31]2[CH:32]=[C:33]([C:43]([CH3:46])=[CH:44][CH:45]=2)[C:34]2[CH:39]=[CH:38][C:37]([C:40]([OH:42])=O)=[CH:36][CH:35]=2)=[O:30])[CH2:27][CH2:26]1.C1C=CC2N(O)N=NC=2C=1.[NH2:57][CH2:58][C:59]([NH:61][CH3:62])=[O:60].CCN(C(C)C)C(C)C>CN(C=O)C>[CH:25]1([NH:28][C:29]([C:31]2[CH:32]=[C:33]([C:34]3[CH:39]=[CH:38][C:37]([C:40]([NH:57][CH2:58][C:59]([NH:61][CH3:62])=[O:60])=[O:42])=[CH:36][CH:35]=3)[C:43]([CH3:46])=[CH:44][CH:45]=2)=[O:30])[CH2:27][CH2:26]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 896752-amino-N-methylacetamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112201515′-[(Cyclopropylamino)carbonyl]-2′-methyl[1,1′-biphenyl]-4-carboxylic acid

Product 1

HCID 69512524HCID 69512524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (65 mg, 0.17 mmol) was added to a solution of {3′-[(cyclopropylamino)carbonyl}-6′-methyl-biphen-4-yl}carboxylic acid (50 mg, 0.17 mmol) in DMF (2 ml). After 5 minutes HOBT (23 mg, 0.17 mmol), 2-amino-N-methylacetamide (0.17 mmol) and DIPEA (0.087 ml, 0.51 mmol) were added and the reaction mixture stirred at room temperature under nitrogen for 18 hours. The DMF was removed in vacuo and the residue partitioned between DCM (5 ml) and aqueous sodium carbonate solution (1M, 5 ml). The organic phase was purified by SPE cartridge (Si, 5 g) eluting in turn with DCM, chloroform, ether, ethyl acetate, acetonitrile, acetone, ethanol, DCM:ethanol:ammonia (40:8:1, 20:8:1 and 10:8:1). The product fractions were concentrated in vacuo to give N3-cyclopropyl-N4′{[(methylamino)carbonyl]methyl}-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue partitioned between DCM (5 ml) and aqueous sodium carbonate solution (1M, 5 ml)
  3. customThe organic phase was purified by SPE cartridge (Si, 5 g)
  4. washeluting in turn with DCM, chloroform, ether, ethyl acetate, acetonitrile, acetone, ethanol, DCM:ethanol:ammonia (40:8:1, 20:8:1 and 10:8:1)
  5. concentrationThe product fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-ec6ada21f9ce4fb4b50f1ac4f60aca26
Source dataset
uspto-grants-2007_04
Patent number
US07208629B2

Reaction notes

Loading…