Diisopropylethylamine → HCID 66561011, compound

HRID 1909974Notes

Reaction equation

HRID 1909974 reaction equation
Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:16]4[C:17]([NH2:21])=[N:18][CH:19]=[CH:20][C:15]=4[O:14][CH:13]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH2:30][C:31](O)=[O:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C)C=O.O>[F:22][C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[CH2:30][C:31]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:16]4[C:17]([NH2:21])=[N:18][CH:19]=[CH:20][C:15]=4[O:14][CH:13]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=[O:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5228232,5-Difluorophenylacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66823748HCID 66823748, compound

Product 1

HCID 66561011HCID 66561011, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine 2HCl (688 mg, 2.016 mmol), 2,5-difluorophenylacetic acid (354 mg, 2.057 mmol), HATU (844 mg, 2.220 mmol), and Hunig's base (1.4 mL, 8.02 mmol) in N,N-Dimethylformamide (DMF) (15 mL) was stirred at room temperature for 17 hr. HPLC indicated complete conversion, so the mixture was poured into water (75 mL), the suspension was stirred for about 10 minutes, and the precipitate was collected by vacuum filtration and dried by suction to give 3-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-amine (834 mg, 2.057 mmol, 102% yield) as a tan solid. LC/MS (ES) m/z=406 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 3.29 (t, J=8.34 Hz, 2H), 3.96 (s, 2H), 4.31 (t, J=8.46 Hz, 2H), 5.52 (s, 2H), 6.93 (d, J=5.81 Hz, 1H), 7.14-7.34 (m, 4H), 7.41 (s, 1H), 7.87 (d, J=5.81 Hz, 1H), 7.92 (s, 1H), 8.13 (d, J=8.08 Hz, 1H).

Workup

  1. stirringthe suspension was stirred for about 10 minutes
  2. filtrationthe precipitate was collected by vacuum filtration
  3. customdried by suction

Sources & evidence

ORD record
ord-6c60482362a14f2fa477d61b3e12bf68
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

Loading…