3,3-Dimethylbutanoyl chloride → HCID 24871517, compound

HRID 1024583Notes

Reaction equation

[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([NH2:15])[C:11]([NH2:14])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[C:18]([CH2:22][C:23](Cl)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(O)C>[NH2:15][C:10]1[CH:9]=[C:8]([O:7][CH2:6][C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)[CH:13]=[CH:12][C:11]=1[NH:14][C:23](=[O:24])[CH2:22][C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 4.5 °C

Procedure

To a solution of 4-(4-fluoro-benzyloxy)-benzene-1,2-diamine (0.23 g, 1 mmol) and N,N-diisopropylethyllamine (0.21 ml, 1.2 mmol) in 8 ml of anhydrous ethanol was added dropwise tert-butylacetylchloride (111 μl, 1 mmol) at 4-5° C. in an ice-water bath. The reaction mixture was stirred for 30 min at 4-5° C. and for 3 hours at room temperature. The solvent was removed in vacuo and the residue was chromatographied (hexane/ethyl acetate, 2:1) to give the desired product as a white solid. 1H-NMR (300 MHz, DMSO-d6): δ 8.94 (brs, 1H, exchangeable with D2O, NH), 7.44 (dd, J=5.7 and 8.7 Hz, 2H), 7.18 (t, J=8.7 Hz, 2H), 6.92 (d, J=8.7 Hz, 1H), 6.34 (d, J=2.7 Hz, 1H), 6.18 (dd, J=8.7 and 2.7 Hz, 1H), 4.95 (s, 2H), 4.79 (brs, 2H, exchangeable with D2O, NH2), 2.13 (s, 2H), 1.00 (s, 9H). MS: 331 (M+1).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-0de8242b358648deb0605f71c06349b5
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722929B2

Reaction notes

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