Diisopropylethylamine → HCID 67125657, compound

HRID 1184925Notes

Reaction equation

[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=O)([CH3:5])[CH3:4])#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[I:46][C:47]1[CH:48]=[C:49]([CH:51]=[CH:52][C:53]=1[CH3:54])[NH2:50]>CN(C=O)C>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([NH:50][C:49]1[CH:51]=[CH:52][C:53]([CH3:54])=[C:47]([I:46])[CH:48]=1)=[O:11])([CH3:4])[CH3:5])#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 3-(2-cyanopropan-2-yl)benzoic acid 3 (2.64 mmol, 500 mg), TBTU (2.77 mmol, 891 mg) and DIPEA (5.29 mmol, 0.873 mL) in DMF (4 mL) was stirred at 50° C. for 15 min. 3-iodo-4-methylaniline (2.77 mmol, 647 mg) was added and stirred overnight at 50° C. Quenched in citric acid solution and extracted with ethyl acetate. Organic layer was washed with brine, dried and evaporated. Purification with chromatography (30% ethyl acetate in heptane) gave 3-(2-cyanopropan-2-yl)-N-(3-iodo-4-methylphenyl)benzamide 111 (861 mg, 81%). NMR (400 MHz, CDCl3) 1.78 (s, 6H), 2.42 (s, 3H), 7.23 (d, J=8.2 Hz, 1H), 7.52 (dd, J=8.2 Hz and 7.4 Hz, 1H), 7.58 (dd, J=8.2 Hz and 2.3 Hz, 1H), 7.71 (dq, J=7.8 Hz and 1.2 Hz), 7.76 (m, 1H), 7.78 (m, 1H), 7.96 (t, J=1.6 Hz, 1H), 8.11 (d, J=2.3 Hz, 1H).

Workup

customQuenched in citric acid solution
extractionextracted with ethyl acetate
washOrganic layer was washed with brine
customdried
customevaporated
customPurification with chromatography (30% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-ff28e03ed5a94239a98f0cf8e0c5f549
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

Loading…