2-Methoxyphenylacetic acid → HCID 53468038, compound

HRID 1909970Notes

Reaction equation

HRID 1909970 reaction equation
Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:20]4[C:15](=[N:16][CH:17]=[N:18][C:19]=4[NH2:21])[N:14]([CH3:22])[N:13]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:31][C:32](O)=[O:33].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=O)C.O>[CH3:22][N:14]1[C:15]2=[N:16][CH:17]=[N:18][C:19]([NH2:21])=[C:20]2[C:12]([C:8]2[CH:7]=[C:6]3[C:11](=[CH:10][CH:9]=2)[N:3]([C:32](=[O:33])[CH2:31][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][CH3:23])[CH2:4][CH2:5]3)=[N:13]1

Participants

7

Reactant 4

HCID 71342-Methoxyphenylacetic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668235503(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl

Product 1

HCID 53468038HCID 53468038, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 20 mL vial with cap, to the solution of 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl (70 mg, 0.206 mmol), [2-(methyloxy)phenyl]acetic acid (34.3 mg, 0.206 mmol), HATU (78 mg, 0.206 mmol) in DMF (2 mL) was added Hunig's base (0.144 mL, 0.825 mmol). The mixture was stirred at room temperature for overnight. LCMS showed reaction was completed. The reaction was poured into water, off-white solid formed. The solid was filtered to give the title compound (78 mg) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.28 (m, 2H), 3.78 (s, 3H), 3.80 (s, 2H), 3.94 (s, 3H), 4.22-4.30 (m, 2H), 6.93 (t, J=7.45 Hz, 1H), 7.01 (d, J=7.83 Hz, 1H), 7.20 (dd, J=7.58, 1.52 Hz, 1H), 7.25-7.32 (m, 1H), 7.43 (d, J=8.34 Hz, 1H), 7.51 (s, 1H), 8.16 (d, J=8.34 Hz, 1H), 8.25 (s, 1H).

Workup

  1. customreaction
  2. customformed
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-fd6876dd28b24f07958db78e183ba72d
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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