1-Hydroxybenzotriazole → HCID 10113609, compound

HRID 747571Notes

Reaction equation

HRID 747571 reaction equation
CN(C(ON1N=NC2[CH:12]=[CH:13][CH:14]=[N:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(C(N[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)CC1.C1C=CC2N([OH:56])N=NC=2C=1.C(O)(=O)C(O)=O.[NH2:63][CH2:64][C:65]1[O:66][C:67]([CH2:70][N:71]([CH3:73])[CH3:72])=[CH:68][CH:69]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:14]1([NH:15][C:10]([C:31]2[CH:32]=[C:33]([C:34]3[CH:35]=[CH:36][C:37]([C:40]([NH:63][CH2:64][C:65]4[O:66][C:67]([CH2:70][N:71]([CH3:73])[CH3:72])=[CH:68][CH:69]=4)=[O:42])=[CH:38][CH:39]=3)[C:43]([CH3:46])=[CH:44][CH:45]=2)=[O:56])[CH2:13][CH2:12]1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59822364HCID 59822364, compoundHCID 69315579515162-21-7

Product 1

HCID 10113609HCID 10113609, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (65 mg, 0.17 mmol) was added to a solution of {3′-[(cyclopropylcarbonyl)amino]-6′-methyl-biphen-4-yl}carboxylic acid (50 mg, 0.17 mmol) in DMF (1 ml). After 5 minutes HOBT (23 mg, 0.17 mmol), 2-aminomethyl-5-(dimethylaminomethyl)furan oxalic acid salt (68 mg, 0.204 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 (10 ml) and aqueous sodium carbonate (1 M, 10 ml). The organic phase wwas reduced to dryness under vacuum and purified by SPE cartridge (Si, 10 g) eluting in turn with DCM, ether, ethyl acetate, acetonitrile, acetone and ethanol to give the N3-cyclopropyl-N4′-({5-[(dimethylamino)methyl]-2-furyl}methyl)-6-methyl-1,1′-biphenyl-3,4′-dicarboxamide (35 mg, 0.081 mmol).

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue partitioned between DCM (10 ml) and aqueous sodium carbonate (1 M, 10 ml)
  3. custompurified by SPE cartridge (Si, 10 g)
  4. washeluting in turn with DCM, ether, ethyl acetate, acetonitrile, acetone and ethanol

Sources & evidence

ORD record
ord-b26b6c991fe645a980c7b42b312f5dea
Source dataset
uspto-grants-2008_07
Patent number
US07396843B2

Reaction notes

Loading…