Diisopropylethylamine → HCID 67979553, compound

HRID 528784Notes

Reaction equation

HRID 528784 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][C:12]2=[C:13]([N:20]3[CH2:23][CH:22]([C:24](O)=[O:25])[CH2:21]3)[N:14]3[C:18]([N:19]=[C:11]2[CH:10]([CH3:29])[CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl-].[CH3:62][C:63]1([CH3:68])[CH2:67][CH2:66][NH2+:65][CH2:64]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][C:12]2=[C:13]([N:20]3[CH2:21][CH:22]([C:24]([N:65]4[CH2:66][CH2:67][C:63]([CH3:68])([CH3:62])[CH2:64]4)=[O:25])[CH2:23]3)[N:14]3[C:18]([N:19]=[C:11]2[CH:10]([CH3:29])[CH2:9]1)=[CH:17][CH:16]=[N:15]3)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67979359HCID 67979359, compoundHCID 178426636HCID 178426636, compound

Product 1

HCID 67979553HCID 67979553, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 300 mg (0.57 mmol) of 10-(3-Carboxy-azetidin-1-yl)-5-methyl-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohept[f]indene-7-carboxylic acid tert-butyl ester (as DIPEA salt) in 6.0 mL DMF was added 484 mg (1.51 mmol) TBTU and 243 μL (1.41 mmol) DIPEA and stirring was continued at room temperature for 30 min. Then 84.3 mg (0.62 mmol) of 3,3-Dimethyl-pyrrolidinium chloride was added and the reaction mixture was stirred additional 4 h. The reaction mixture was filtered and the purified by HPLC.

Workup

  1. stirringthe reaction mixture was stirred additional 4 h
  2. filtrationThe reaction mixture was filtered
  3. customthe purified by HPLC

Sources & evidence

ORD record
ord-77631a84fef7438483d07a6be0c9b13b
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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