Diisopropylethylamine → HCID 53469265, compound

HRID 1910079Notes

Reaction equation

HRID 1910079 reaction equation
[Cl:1][C:2]1[C:3]2[O:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[NH:17][CH2:16][CH2:15]4)[C:4]=2[C:5]([NH2:8])=[N:6][CH:7]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[CH2:29][C:30](O)=[O:31].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>[Cl:1][C:2]1[C:3]2[O:11][CH:10]=[C:9]([C:12]3[CH:13]=[C:14]4[C:18](=[CH:19][CH:20]=3)[N:17]([C:30](=[O:31])[CH2:29][C:23]3[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=3[F:21])[CH2:16][CH2:15]4)[C:4]=2[C:5]([NH2:8])=[N:6][CH:7]=1

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 66823589HCID 66823589, compound

Product 1

HCID 53469265HCID 53469265, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7-chloro-3-(2,3-dihydro-1H-indol-5-yl)furo[3,2-c]pyridin-4-amine (58.9 mg, 0.206 mmol), (2,5-difluorophenyl)acetic acid (35.5 mg, 0.206 mmol), HATU (78 mg, 0.206 mmol), and DIEA (0.036 mL, 0.206 mmol) in N,N-Dimethylformamide (DMF) (3 mL) was stirred overnight at room temperature. LCMS analysis at this time indicated good conversion, so the reaction mixture was poured into water (10 mL) and stirred for one hour. The resulting precipitate was collected by filtration, dried at the pump for an hour, adsorbed onto silica and purified by flash chromatography (0-10% MeOH in EtOAc) to afford 7-chloro-3-{1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}furo[3,2-c]pyridin-4-amine (67 mg, 73.9% yield) as a white solid. LC-MS (ES) m/z=440, 442 [M+H]+. 1H NMR (400 MHz, DMSO-d6) ppm 3.29 (t, J=8.46 Hz, 2H), 3.96 (s, 2H), 4.31 (t, J=8.34 Hz, 2H), 5.72 (s, 2H), 7.13-7.34 (m, 4H), 7.41 (s, 1H), 7.92 (s, 1H), 8.07 (s, 1H), 8.13 (d, J=8.34 Hz, 1H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried at the pump for an hour
  3. custompurified by flash chromatography (0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-c55a76279c90448fb110d628247dbd13
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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