Acryloyl chloride → HCID 178460005, compound

HRID 64335Notes

Reaction equation

HRID 64335 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7]3[N:8]([N:9]=[C:10]([C:15]4[CH:20]=[CH:19][C:18]([O:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:17][CH:16]=4)[C:11]=3[C:12]([NH2:14])=[O:13])[C:4]=2[CH:3]=1.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32]>C(Cl)Cl>[C:30]([NH:1][C:2]1[CH:29]=[CH:28][C:5]2[NH:6][C:7]3[N:8]([N:9]=[C:10]([C:15]4[CH:16]=[CH:17][C:18]([O:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:19][CH:20]=4)[C:11]=3[C:12]([NH2:14])=[O:13])[C:4]=2[CH:3]=1)(=[O:33])[CH:31]=[CH2:32]

Participants

4

Reactant 2

HCID 13140Acryloyl chlorideHCID 178513488HCID 178513488, compound

Product 1

HCID 178460005HCID 178460005, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-amino-2-(4-phenoxyphenyl)-4H-benzo[4,5]imidazo[1,2-b]pyrazole-3-carboxamide (45 mg, 0.11 mmol) in 10 mL of DCM at 0° C. was added TEA (36 mg, 0.35 mmol). Acryloyl chloride (11 mg, 0.12 mmol) in 2 mL of DCM was added dropwise over a period of 20 min. The mixture was stirred until TLC and LCMS analysis showed that most of starting material was consumed. The mixture was then partitioned between water (50 mL) and DCM (20 mL), extracted with additional 20 mL of DCM. The combined organic layer was washed with brine, dried over Na2SO4, concentrated and purified by Pre-TLC (DCM/MeOH=20/1) to get 4 mg (7.8%) of 7-acrylamido-2-(4-phenoxyphenyl)-4H-benzo[4,5]imidazo[1,2-b]pyrazole-3-carboxamide as a grey solid. 1H NMR (400 MHz, CD3OD-d4) δ 8.25 (s, 1H), 7.61 (d, J=8.4 Hz, 2H), 7.44 (d, J=8.8 Hz, 1H), 7.39 (d, J=8.8 Hz, 1H), 7.32 (d, J=7.6 Hz, 1H), 7.30 (d, J=7.6 Hz, 1H), 7.08 (t, J=7.6 Hz, 1H), 7.05-6.90 (m, 4H), 6.42-6.25 (m, 2H), 5.69 (dd, J=9.6, 1.9 Hz, 1H). MS (ESI) m/e [M+1]+ 438.

Workup

  1. customwas consumed
  2. customThe mixture was then partitioned between water (50 mL) and DCM (20 mL)
  3. extractionextracted with additional 20 mL of DCM
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by Pre-TLC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-c712a1d7e0054d08a056579554e6b55a
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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