Oxalyl chloride → HCID 86692291, compound

HRID 1469828Notes

Reaction equation

HRID 1469828 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:7][CH2:6][CH:5]([O:8][C:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[C:14]([NH2:19])[C:13]=3[CH:12]=[CH:11][N:10]=2)[CH2:4][CH2:3]1.[Cl:21][C:22]1[C:27]([C:28](O)=[O:29])=[C:26]([F:31])[C:25]([CH2:32][NH:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:24][CH:23]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:21][C:22]1[C:27]([C:28]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[CH:12]=[CH:11][N:10]=[C:9]3[O:8][CH:5]2[CH2:6][CH2:7][C:2]([CH3:20])([CH3:1])[CH2:3][CH2:4]2)=[O:29])=[C:26]([F:31])[C:25]([CH2:32][NH:33][C:34](=[O:39])[C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 71678215HCID 71678215, compound

Product 1

HCID 86692291HCID 86692291, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 1-((4,4-dimethylcyclohexyl)oxy)isoquinolin-5-amine (Intermediate-28, 70 mg, 0.25 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 89 mg, 0.31 mmol), oxalyl chloride (59 mg, 0.47 mmol), DMF (1 drop) and DIPEA (97 mg, 0.75 mmol) in CH2Cl2 (3 mL) to afford 45 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.89 (s, 1H), 8.19 (t, 1H), 8.14 (d, J=8.4 Hz, 1H), 8.04 (d, J=5.7 Hz, 1H), 7.95 (d, J=7.8 Hz, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.48 (d, J=6.0 Hz, 1H), 7.43 (s, 1H), 7.37 (d, J=7.8 Hz, 1H), 5.28 (m, 1H), 4.34 (d, J=5.4 Hz, 2H), 1.90 (m, 2H), 1.78 (m, 2H), 1.53 (m, 2H), 1.34 (m, 2H), 1.15 (s, 9H), 1.00 (s, 3H), 0.97 (s, 3H); MS (m/z): 540.10 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6094d0e4818e4e6e996db5fa12aed43b
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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