Oxalyl chloride → HCID 71679221, compound

HRID 1469825Notes

Reaction equation

HRID 1469825 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:7][CH2:6][CH:5]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH2:19])[CH:15]=[CH:16][CH:17]=3)[N:12]=[C:11]([C:20]([F:23])([F:22])[F:21])[N:10]=2)[CH2:4][CH2:3]1.[Cl:25][C:26]1[C:31]([C:32](O)=[O:33])=[C:30]([F:35])[C:29]([CH2:36][NH:37][C:38](=[O:43])[C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:28][CH:27]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:25][C:26]1[C:31]([C:32]([NH:19][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[N:12]=[C:11]([C:20]([F:23])([F:21])[F:22])[N:10]=[C:9]3[NH:8][CH:5]2[CH2:4][CH2:3][C:2]([CH3:24])([CH3:1])[CH2:7][CH2:6]2)=[O:33])=[C:30]([F:35])[C:29]([CH2:36][NH:37][C:38](=[O:43])[C:39]([CH3:41])([CH3:40])[CH3:42])=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584833746-Chloro-2-fluoro-3-(pivalamidomethyl)benzoic acidHCID 86692289HCID 86692289, compound

Product 1

HCID 71679221HCID 71679221, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared following the procedure described in Example-1 using N4-(4,4-dimethylcyclohexyl)-2-(trifluoromethyl)quinazoline-4,8-diamine (Intermediate-26, 100 mg, 0.295 mmol), 6-chloro-2-fluoro-3-(pivalamidomethyl)benzoic acid (Intermediate-2, 127 mg, 0.443 mmol), oxalyl chloride (84 mg, 0.66 mmol), DMF (1 drop) and DIPEA (115 mg, 0.89 mmol) in CH2Cl2 (3 mL) to afford 35 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.30 (s, 1H), 8.67-8.65 (d, J=7.2 Hz, 1H), 8.59-8.56 (d, J=8.1 Hz, 1H), 8.22-8.16 (m, 2H), 7.74-7.68 (t, J=8.4 Hz, 1H), 7.45-7.33 (m, 2H), 4.32-4.30 (d, J=5.4 Hz, 2H), 4.14 (m, 1H), 1.76-1.66 (m, 4H), 1.43-1.24 (m, 4H), 1.14 (s, 9H), 0.99 (s, 3H), 0.95 (s, 3H); MS (m/z): 608.38 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-0bfe25b0b0c64d1f82d1757e10b55b1a
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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