Benzylamine → 6-benzyl-4-(3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

HRID 41882Notes

Reaction equation

HRID 41882 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]4[CH2:19][O:20][C:21](=[O:22])[C:14]=34)=[CH:11][N:10]([CH3:23])[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(=O)C>[CH2:24]([N:31]1[C:21](=[O:22])[C:14]2[C:15](=[N:16][CH:17]=[CH:18][C:13]=2[C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][N:10]([CH3:23])[CH:11]=2)[C:19]1=[O:20])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 679718214-[3-(4-Fluorophenyl)-1-methyl-1H-pyrazol-4-yl]furo[3,4-b]pyridin-5(7H)-one

Product 1

HCID 679717066-benzyl-4-(3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-[3-(4-Fluorophenyl)-1-methyl-1H-pyrazol-4-yl]furo[3,4-b]pyridin-5(7H)-one (Example 1, step 5, 472 mg, 1.46 mmol) and benzyl amine (0.167 mL, 1.53 mmol) in acetic acid (4.7 mL) were heated at reflux for 18 hr, cooled and then concentrated to a brown solid. This material was stirred with diethyl ether (20 mL) for 10 min and then filtered to yield 450 mg (75%) of Ex 5-Step 1 product as a tan colored solid: LCMS m/z 413.5 (M+1); 1H NMR (400 MHz, CDCl3) δ 8.57 (d, J=5.2, 1H), 8.15 (s, 1H), 7.26-7.42 (m, 7H), 7.13 (d, J=5.3, 1H), 7.01 (dd, J=8.6, 8.6, 2H), 4.87 (s, 2H), 4.00 (s, 3H).

Workup

  1. temperatureat reflux for 18 hr
  2. temperaturecooled
  3. concentrationconcentrated to a brown solid
  4. filtrationfiltered
  5. customto yield 450 mg (75%) of Ex 5-Step 1 product as a tan colored solid

Sources & evidence

ORD record
ord-ce316869c633465c80d5bba21a1b3c64
Source dataset
uspto-grants-2013_09
Patent number
US08536164B2

Reaction notes

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