Diisopropylethylamine → HCID 21874350, compound

HRID 723453Notes

Reaction equation

HRID 723453 reaction equation
Cl.[Br-].[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][C:12]2[C:17]3=[C:18]([CH2:21][N+](CC)(CC)CC)[CH:19]=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)[CH:7]=[CH:8][C:9]=1[F:10].Cl.[Cl:30][CH2:31][CH2:32][NH:33][CH2:34][CH2:35][Cl:36].CCN(C(C)C)C(C)C>CC#N>[Cl:30][CH2:31][CH2:32][N:33]([CH2:21][C:18]1[CH:19]=[CH:20][N:16]2[C:17]=1[C:12]([NH:11][C:6]1[CH:7]=[CH:8][C:9]([F:10])=[C:4]([Cl:3])[CH:5]=1)=[N:13][CH:14]=[N:15]2)[CH2:34][CH2:35][Cl:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 21874296HCID 21874296, compound

Product 1

HCID 21874350HCID 21874350, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of Compound 1E (50 mg, 0.1 mmol), bis-(2-chloroethyl)amine hydrochloride (18 mg, 0.1 mmol), DIEA (36 μl, 0.2 mmol) in CH3CN (0.5 ml) was heated to 60° C. for 3 h. The mixture was cooled to rt and concentrated to give Compound 133A which was used directly in next step. 133A had an analytical HPLC retention time=2.986 min. (Chromolith SpeedROD 4.6×50 mm, 10–90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 ml/min, monitoring at 220 nm) and a LC/MS M++1=416.

Workup

  1. temperatureThe mixture was cooled to rt
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dad7b35a695e4038af75f67ed1d6df24
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

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