Diisopropylethylamine → HCID 66706295, compound

HRID 1470656Notes

Reaction equation

HRID 1470656 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11].[C:13]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14](C2C(C(O)=O)=CC=CC=2)=[CH:15][CH:16]=[CH:17][CH:18]=1.CN([C:37]([O:41]N1N=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=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:37]([C:31]2[CH:30]=[CH:29][C:28]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:33][CH:32]=2)=[O:41])[C:5]=1[NH2:11]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5718252,3-Diaminobenzoic acid methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 19933666HCID 19933666, compound

Product 1

HCID 66706295HCID 66706295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,3-diamino-benzoic acid methyl ester (200 mg, 1.2 mmol), biphenyl benzoic acid (238 mg, 1.2 mmol), HATU (1.14 g, 3 mmol) in dry DMF (5 mL) was added diisopropylethyl amine (0.6 mL, 3.6 mmol). The mixture was stirred at ambient temperature overnight then poured into water (50 mL). The precipitated solid was filtered and dried in a vacuum oven to afford the required compound, which was used directly for the next step without any purification (300 mg, 72%).

Workup

  1. filtrationThe precipitated solid was filtered
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-a2114f4a27dc484982a29bbd326d35fc
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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