Diisopropylethylamine → HCID 59851365, compound

HRID 545003Notes

Reaction equation

HRID 545003 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24]([C:27](O)=[O:28])[CH:25]=[CH:26][C:17]=4[C:16]=3[N:30]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:62][CH2:63][CH2:64][NH:65][C:66](=[O:72])[O:67][C:68]([CH3:71])([CH3:70])[CH3:69]>CN(C=O)C.O>[C:68]([O:67][C:66](=[O:72])[NH:65][CH2:64][CH2:63][NH:62][C:27]([C:24]1[CH:25]=[CH:26][C:17]2[C:16]3[N:30]=[C:12]([NH:11][C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:13]=[CH:14][C:15]=3[CH2:21][C:20](=[O:22])[NH:19][C:18]=2[CH:23]=1)=[O:28])([CH3:69])([CH3:71])[CH3:70]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 187201N-BOC-ethylenediamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59851270HCID 59851270, compound

Product 1

HCID 59851365HCID 59851365, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2-(3,4-dimethoxy-phenylamino)-6-oxo-6,7-dihydro-5H-benzo[b]pyrimido[4,5-d]azepine-9-carboxylic acid (I-53) (75 mg, 0.18 mmol) in DMF (5 mL) was added N,N-diisopropylethylamine (0.10 mL, 0.55 mmol), TBTU (65 mg, 0.20 mmol), and tert-butyl 2-aminoethylcarbamate (35.5 mg, 0.22 mmol). The reaction stirred at 22° C. overnight. The reaction mixture was diluted with H2O, and the precipitate that formed was filtered, washed with H2O and dried to give I-71-a [MS m/z=549 (M+H)] which was carried on crude to the deprotection.

Workup

  1. customthe precipitate that formed
  2. filtrationwas filtered
  3. washwashed with H2O
  4. customdried
  5. customto give I-71-a [MS m/z=549 (M+H)] which

Sources & evidence

ORD record
ord-476a7b1b5e3f4239bf890065d6228327
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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