Dichloromethane → HCID 68814957, compound

HRID 2105002Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4](C(Cl)C2C=CC=C(CC)C=2)[N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.CC[N:38]([CH:42]([CH3:44])[CH3:43])[CH:39]([CH3:41])C.N[C:46]1[CH:53]=[CH:52][C:49]([C:50]#N)=[CH:48][CH:47]=1.C(Cl)Cl>CC#N.CCOC(C)=O>[Br:1][C:2]1[N:3]=[C:4]([N:38]([CH2:39][C:41]2[CH:46]=[CH:53][CH:52]=[C:49]([CH2:48][CH3:47])[CH:50]=2)[C:42]2[CH:43]=[CH:13][C:8]([C:7]#[N:5])=[CH:9][CH:44]=2)[N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of the chloro intermediate (0.382 mmol) in 3 mL CH3CN at rt, was added DIEA (0.133 mL, 0.764 mmol), 4-aminobenzonitrile (67.7 mg, 0.573 mmol) and 1 mL CH2Cl2. The mixture was stirred at 50° C. for 3 h, then was diluted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (O to 50% EtOAc/hexanes gradient) to afford 225 mg of Intermediate 175.3 as a colorless oil. LCMS (4 min gradient, 50 to 100% B, A=95% H2O/5% CH3CN/0.1% TFA, B=95% CH3CN/5% H2O/0.1% TFA) RT=5.20 min, 623.13 (M+H)+.

Workup

washThe organic phase was washed with H2O and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe crude product was purified by flash chromatography (O to 50% EtOAc/hexanes gradient)

Sources & evidence

ORD record: ord-288a3cbde76046238bf7ed3472f2595a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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