Ethanolamine → HCID 56953206, compound

HRID 2366216Notes

Reaction equation

HRID 2366216 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:27])[C:9]=1[C:10]1[S:11][C:12]2[C:13]([NH:19][C:20]3[CH:25]=[C:24](Cl)[N:23]=[CH:22][N:21]=3)=[N:14][CH:15]=[CH:16][C:17]=2[N:18]=1)[C:5]#[N:6].[CH2:28]([CH2:30][NH2:31])[OH:29]>CN1C(=O)CCC1>[Cl:27][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[C:9]=1[C:10]1[S:11][C:12]2[C:13]([NH:19][C:20]3[CH:25]=[C:24]([NH:31][CH2:30][CH2:28][OH:29])[N:23]=[CH:22][N:21]=3)=[N:14][CH:15]=[CH:16][C:17]=2[N:18]=1)[C:5]#[N:6]

Participants

4

Reactant 2

HCID 700Ethanolamine2×HCID 86668995HCID 86668995, compound

Product 1

HCID 56953206HCID 56953206, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 3,5-dichloro-4-[4-(6-chloropyrimidin-4-ylamino)-thiazolo[5,4-c]pyridin-2-yl]-benzonitrile (0.030 g, 0.07 mmol) and ethanolamine (12.6 μL, 0.21 mmol) in NMP (0.7 mL) was subjected to microwave irradiation at 150° C. for 75 minutes. Further ethanolamine (5.0 μL, 0.08 mmol) was added and the mixture subjected to microwave irradiation at 160° C. for 45 minutes then 190° C. for 45 minutes. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge that was washed with MeOH and the product eluted with 2M ammonia in MeOH. The relevant fractions were combined and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-5% MeOH in DCM) to give the desired compound as an off-white solid (0.014 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.13 (s, 1H), 8.40-8.34 (m, 3H), 8.16 (s, 1H), 7.73 (d, J=5.6 Hz, 1H), 7.22 (br s, 1H), 6.85 (br s, 1H), 4.72 (t, J=5.4 Hz, 1H), 3.52 (q, J=5.9 Hz, 3H). LCMS (Method C): RT=3.10 min, m/z: 458 [M+H+].

Workup

  1. customirradiation at 150° C. for 75 minutes
  2. customirradiation at 160° C. for 45 minutes
  3. washwas washed with MeOH
  4. washthe product eluted with 2M ammonia in MeOH
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (0-5% MeOH in DCM)

Sources & evidence

ORD record
ord-6e27690c66034a78abb5e5cd0786614e
Source dataset
uspto-grants-2014_04
Patent number
US08697708B2

Reaction notes

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