Diisopropylethylamine → N-(5-(4-(4-Cyanophenyl)azepane-1-carbonyl)-2-methylphenyl)-6-fluoronicotinamide

HRID 541219Notes

Reaction equation

HRID 541219 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:6].C(N(CC)C(C)C)(C)C.[F:35][C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][N:37]=1>ClCCl>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][N:7]([C:5]([C:4]3[CH:22]=[CH:23][C:24]([CH3:25])=[C:2]([NH:1][C:40](=[O:41])[C:39]4[CH:43]=[CH:44][C:36]([F:35])=[N:37][CH:38]=4)[CH:3]=3)=[O:6])[CH2:8][CH2:9]2)=[CH:15][CH:16]=1)#[N:19]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 146236022-Fluoropyridine-5-carbonyl chlorideHCID 682889154-(1-(3-Amino-4-methylbenzoyl)azepan-4-yl)benzonitrile2×

Product 1

HCID 68288115N-(5-(4-(4-Cyanophenyl)azepane-1-carbonyl)-2-methylphenyl)-6-fluoronicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a 4-mL vial containing 4-(1-(3-amino-4-methylbenzoyl)azepan-4-yl)benzonitrile (compound 40.5, 44 mg, 0.13 mmol, 1.0 equiv) was added dichloromethane (1 mL) and N,N-diisopropylethylamine (35 μL, 0.20 mmol, 1.5 equiv). A solution of 6-fluoronicotinoyl chloride (22 mg, 0.14 mmol, 1.05 equiv) in dichloromethane (1 mL) was added dropwise over about 2 minutes. The resulting mixture was stirred at room temperature for 19 hours then diluted with dichloromethane (5 mL) and washed with 1 M NaH2PO4 (3 mL), saturated sodium bicarbonate (3 mL) and brine (3 mL). The organics were dried (Na2SO4), filtered and concentrated to obtain the title compound as a brown wax (64 mg, theoretical). m/z (ES+) 457 (M+H)+.

Workup

  1. washwashed with 1 M NaH2PO4 (3 mL), saturated sodium bicarbonate (3 mL) and brine (3 mL)
  2. dry with materialThe organics were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2dae948586cd4b149126482931c9f9b3
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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