HCID 58902360, compound → HCID 58902401, compound

HRID 1640187Notes

Reaction equation

HRID 1640187 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:13][C:14]([CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:26][C:27]4[CH:32]=[CH:31][N:30]=[C:29]([C:33]([N:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)=[O:34])[CH:28]=4)=[CH:21][CH:22]=3)[CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)#[N:2]>N.CO.[Ni]>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([NH:13][C:14]([CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([O:26][C:27]4[CH:32]=[CH:31][N:30]=[C:29]([C:33]([N:35]5[CH2:36][CH2:37][CH2:38][CH2:39]5)=[O:34])[CH:28]=4)=[CH:21][CH:22]=3)[CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

5

Reactant 1

HCID 58902360HCID 58902360, compound

Product 1

HCID 58902401HCID 58902401, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of N-[3-cyano-5-(trifluoromethyl)phenyl]-7-{[2-(pyrrolidin-1-ylcarbonyl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide (0.310 g, 0.58 mmol) and Raney Ni (50% v/v in water, 2.0 mL) in 7M ammonia in MeOH (30 mL) was allowed to stir at rt under an atmosphere of hydrogen overnight. The reaction mixture was filtered over Celite, the Celite rinsed with MeOH, and the solution concentrated to give N-[3-(aminomethyl)-5-(trifluoromethyl)phenyl]-7-{[2-(pyrrolidin-1-ylcarbonyl)pyridin-4-yl]oxy}-1,2,3,4-tetrahydronaphthalene-2-carboxamide I-362 (0.205 g, 55%). 1H NMR (400 MHz, CD3OD, HCl Salt) δ: 8.69 (d, 1H), 8.08 (s, 1H), 8.02 (s, 1H), 7.70 (d, 1H), 7.54 (s, 1H), 7.45-7.42 (dd, 1H), 7.31 (d, 2H), 7.09-7.03 (m, 2H), 4.20 (s, 2H), 3.65-3.59 (m, 4H), 3.15-2.91 (m, 5H), 2.25-2.21 (m, 1H), and 2.02-1.93 (m, 5H). LCMS: (FA) ES+ 539.8, ES− 537.5.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. washthe Celite rinsed with MeOH
  3. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-5b673cf1c4354bbcb6d37d89d442fdab
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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