Diisopropylethylamine → HCID 71542164, compound

HRID 1402557Notes

Reaction equation

HRID 1402557 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[NH:17][CH:16]=[C:15]([C:18](O)=[O:19])[CH:14]=3)[CH:8]=2)=[CH:4][C:3]=1[NH:23][C:24]([C:26]1[O:27][CH:28]=[CH:29][C:30]=1[CH3:31])=[O:25].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:65][CH2:66][CH2:67][CH:68]([O:72][CH2:73][CH3:74])[O:69][CH2:70][CH3:71]>CN(C=O)C.O>[CH2:70]([O:69][CH:68]([O:72][CH2:73][CH3:74])[CH2:67][CH2:66][NH:65][C:18]([C:15]1[CH:14]=[C:13]([C:9]2[CH:8]=[C:7]([O:6][C:5]3[CH:21]=[CH:22][C:2]([F:1])=[C:3]([NH:23][C:24]([C:26]4[O:27][CH:28]=[CH:29][C:30]=4[CH3:31])=[O:25])[CH:4]=3)[CH:12]=[CH:11][N:10]=2)[NH:17][CH:16]=1)=[O:19])[CH3:71]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5210291-Amino-3,3-diethoxypropaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 51001711HCID 51001711, compound

Product 1

HCID 71542164HCID 71542164, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-(4-{4-fluoro-3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrole-3-carboxylic acid (300 mg, 0.71 mmol) in 10 ml of anhydrous DMF were added HATU (324 mg, 0.85 mmol) and N,N-diisopropylethylamine (200 mg, 1.55 mmol). The mixture was stirred at room temperature for 10 minutes, followed by addition of 1-amino-3,3-diethoxypropane (157 mg, 1.06 mmol), and stirring was continued for another 10 minutes. The mixture was poured into 100 ml of water with vigorous stirring. The precipitates were filtered, washed with water and dried in vacuo to give N-(3,3-diethoxypropyl)-5-(4-{4-fluoro-3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrole-3-carboxamide as white solid. Yield: 380 mg, 97%.

Workup

  1. stirringstirring
  2. waitwas continued for another 10 minutes
  3. filtrationThe precipitates were filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-74496a357f58471693e7b427f0acadb0
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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