Oxalyl chloride → HCID 86692292, compound

HRID 1469830Notes

Reaction equation

HRID 1469830 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:3]=1[O:4][C:5]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([NH2:15])[C:9]=2[CH:8]=[CH:7][N:6]=1.[Cl:24][C:25]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:30][C:26]=1[C:27](O)=[O:28].C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:24][C:25]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:36](=[O:41])[C:37]([CH3:39])([CH3:38])[CH3:40])=[CH:30][C:26]=1[C:27]([NH:15][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][N:6]=[C:5]2[O:4][C:3]1[CH:16]=[C:17]([C:20]([F:21])([F:23])[F:22])[CH:18]=[CH:19][C:2]=1[F:1])=[O:28]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 86692247HCID 86692247, compound

Product 1

HCID 86692292HCID 86692292, compoundYield 25.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using 1-(2-fluoro-5-(trifluoromethyl)phenoxy)isoquinolin-5-amine (Intermediate-36, 80 mg, 0.24 mmol), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 134 mg, 0.49 mmol), oxalyl chloride (93 mg, 0.74 mmol), DMF (1 drop) and DIPEA (93 mg, 0.72 mmol) in CH2Cl2 (5 mL) to afford 35 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.77 (s, 1H), 8.32 (d, 1H), 8.11 (t, 1H), 8.09 (d, 1H), 8.00-7.96 (m, 2H), 7.75-7.69 (m, 4H), 7.55 (m, 2H), 7.38 (d, 1H), 4.32 (d, J=5.4 Hz, 2H), 1.14 (s, 9H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6abdb99f886f4aa09284f701dac34499
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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