Methanimidamide, hydrochloride (1:1) → HCID 136500838, compound

HRID 1055855Notes

Reaction equation

HRID 1055855 reaction equation
Cl.[CH:2](N)=[NH:3].[NH2:5][C:6]1[NH:7][C:8]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[C:23]([Cl:26])[CH:22]=[CH:21]3)=[CH:9][C:10]=1[C:11]([O:13]CC)=O>CC(O)C>[ClH:26].[Cl:26][C:23]1[CH:22]=[CH:21][C:20]2[C:25](=[C:16]([C:8]3[NH:7][C:6]4[N:5]=[CH:2][NH:3][C:11](=[O:13])[C:10]=4[CH:9]=3)[CH:17]=[CH:18][CH:19]=2)[N:24]=1

Participants

4

Reactant 2

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 89783934HCID 89783934, compound

Product 1

HCID 136500838HCID 136500838, compoundYield 178%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Conditions

Temperature
100 °C

Procedure

Formamidine hydrochloride (0.296 g, 3.67 mmol) and ethyl 2-amino-5-(2-chloroquinolin-8-yl)-1H-pyrrole-3-carboxylate (0.232 g, 0.735 mmol) were combined in 3 mL IPA, sealed, and heated to 100° C. overnight. An additional 1 mL IPA was added, and the reaction resealed and heated to 110° C. for 24 additional hours. The reaction was cooled, diluted with IPA, and filtered, rinsing 2×IPA. The solid was collected and dried in vacuo to give 6-(2-chloroquinolin-8-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one hydrochloride (0.218 g, 0.654 mmol, 89% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 12.34 (1H, br. s.), 8.53 (1H, d, J=8.6 Hz), 8.23-8.30 (1H, m), 8.00 (1H, dd, J=7.9, 1.1 Hz), 7.92 (1H, s), 7.66-7.77 (2H, m), 7.49 (1H, s), 7.01-7.26 (2H, m). m/z (ESI, +ve) 296.9 (M+H)+.

Workup

  1. customsealed
  2. customthe reaction resealed
  3. temperatureheated to 110° C. for 24 additional hours
  4. temperatureThe reaction was cooled
  5. filtrationfiltered
  6. washrinsing 2×IPA
  7. customThe solid was collected
  8. customdried in vacuo

Sources & evidence

ORD record
ord-bcc97e364f3c4593a7bc1bf3634a790d
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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