Ethyl Acrylate → HCID 67111859, compound

HRID 1177650Notes

Reaction equation

HRID 1177650 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[S:11][C:12]4[C:17]([N:18]=3)=[CH:16][CH:15]=[C:14]([C:19]3([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[CH2:21][CH2:20]3)[N:13]=4)=[CH:9][C:4]=2[N:3]=[CH:2]1.CN1CCCN2C1=NCCC2.[C:39]([O:43][CH2:44][CH3:45])(=[O:42])[CH:40]=[CH2:41]>C(#N)C>[C:22]1([C:19]2([C:14]3[N:13]=[C:12]4[S:11][C:10]([C:8]5[CH:7]=[CH:6][C:5]6[N:1]([CH2:41][CH2:40][C:39]([O:43][CH2:44][CH3:45])=[O:42])[CH:2]=[N:3][C:4]=6[CH:9]=5)=[N:18][C:17]4=[CH:16][CH:15]=3)[CH2:20][CH2:21]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8821Ethyl AcrylateHCID 1235837-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-eneHCID 178420040HCID 178420040, compound

Product 1

HCID 67111859HCID 67111859, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-(1H-benzo[d]imidazol-5-yl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (100 mg, 0.271 mmol) was added acetonitrile (2.7 mL) before 7-methyl-1,5,7-triazabicyclo(4.4.0)dec-5-ene (1.949 μL, 0.014 mmol) and ethyl acrylate (36.2 μL, 0.326 mmol) were added and stirred at ambient temperature for 2 h to give a 2:1 mixture of regioisomers. Ethyl 3-(5-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)-1H-benzo[d]imidazol-1-yl)propanoate was obtained after regioisomer separation via SFC (Column: ChiralPak AD-H; Mobile Phase: 50:50 liquid CO2/isopropanol with 0.2% isopropylamine). MS (ESI) m/z: Calculated: 468.2; Observed: 469.2 (M++H).

Workup

  1. additionwere added
  2. customto give
  3. additiona 2:1 mixture of regioisomers

Sources & evidence

ORD record
ord-c3ab08a0b798493f8bf658bd536f8682
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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