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Diisopropylethylamine → HCID 178433061, compound

HRID 244041
Notes
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Reaction equation

HRID 244041 reaction equation
[N:1]1[N:2]=[C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]([N:14]2[CH2:21][CH:20]3[CH:16]([CH2:17][NH:18][CH2:19]3)[CH2:15]2)=[O:13])[NH:4][CH:5]=1.Cl[C:23]1[N:28]=[C:27]([CH3:29])[C:26]([CH3:30])=[C:25]([CH3:31])[N:24]=1.CCN(C(C)C)C(C)C>C(#N)C>[N:1]1[N:2]=[C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]([N:14]2[CH2:15][CH:16]3[CH:20]([CH2:19][N:18]([C:23]4[N:28]=[C:27]([CH3:29])[C:26]([CH3:30])=[C:25]([CH3:31])[N:24]=4)[CH2:17]3)[CH2:21]2)=[O:13])[NH:4][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 125019872-Chloro-4,5,6-trimethylpyrimidineHCID 178519509HCID 178519509, compound

Product 1

HCID 178433061HCID 178433061, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The product of Step A (167 mg, 0.421 mmol), Intermediate 56 (66 mg, 0.421 mmol) and DIPEA (0.29 mL, 1.68 mmol) were heated for 2 h at 200° C. in ACN (1.4 mL) in the microwave. The mixture was concentrated in vacuo. The crude product was purified using Agilent HPLC (basic system) to yield impure material. This material was subsequently purified using normal phase chromatography (DCM to 8% 2M NH3 in MeOH/DCM) to afford the title compound (49 mg, 29%). MS (ESI) mass calculated for C22H25N7O, 403.49; m/z found, 404.2. 1H NMR (500 MHz, CDCl3): 8.16 (d, J=7.8 Hz, 1H), 8.06 (s, 1H), 7.54-7.49 (m, 1H), 7.48-7.44 (m, 1H), 7.35 (d, J=7.5 Hz, 1H), 3.96-3.89 (m, 1H), 3.85-3.77 (m, 1H), 3.74-3.68 (m, 1H), 3.68-3.55 (m, 2H), 3.42 (br s, 2H), 3.16 (br s, 1H), 3.04-2.96 (m, 1H), 2.89 (br s, 1H), 2.32 (s, 6H), 2.05 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe crude product was purified
  3. customto yield impure material
  4. customThis material was subsequently purified

Sources & evidence

ORD record
ord-7a40ab39d2784a03b09e7ac2ebec0369
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes