Dichloromethane → HCID 10094164, compound

HRID 1437455Notes

Reaction equation

[I-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]1[CH2:11][CH2:12][N:13]([C:23]([N:25]2[CH:29]=C[N+](C)=[CH:26]2)=[O:24])[CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[CH:15]=1.CC[N:33]([CH2:36][CH3:37])[CH2:34]C.[CH2:38](Cl)Cl>>[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]1[CH2:11][CH2:12][N:13]([C:23]([N:25]([CH3:26])[CH2:29][CH:37]([CH3:38])[CH2:36][NH:33][CH3:34])=[O:24])[CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[CH:15]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 86603604HCID 86603604, compound

Product 1

HCID 10094164HCID 10094164, compound

Procedure

To a crude solution of 3-2 (25 mg, 0.05 mmol) in CH2Cl2 (1 mL) was added Et3N (0.02 mL, 0.14 mmol) and amine (11 mg, 0.09 mmol) and the reaction stirred overnight. The reaction was simply concentrated and purification was conducted by reverse phase column chromatography (CH3CN/H2O/0.1% TFA gradient). 1H NMR (300 MHz, CDCl3) rotamers δ 7.30-6.80 (m, 7H), 6.10 (s, 1H), 5.58 (br s, 1H), 4.08 (m, 1H), 3.58 (m, 2H), 3.46 (s, 3H), 3.30 (m, 1H), 2.90 (m, 2H), 2.58 (m, 2H), 2.38 (s, 3H), 1.90 (s, 3H), 1.00 (m, 1H); MS 430.4 observed, 430.5 required (M+H+).

Workup

concentrationThe reaction was simply concentrated
custompurification

Sources & evidence

ORD record: ord-e6d7abc54b1d486c888ee04ef2e979b5
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622489B2

Reaction notes

Loading…