Triethylamine → HCID 178518225, compound

HRID 510147Notes

Reaction equation

HRID 510147 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]C)=O)=[CH:6][N:5]=[C:4]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])[N:13]=2)[N:3]=1.Cl.[CH:30]([NH2:32])=[NH:31].C(N(CC)CC)C>CN(C=O)C>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][N:14]1[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:20]2[C:12]([C:4]2[N:3]=[C:2]3[NH:32][CH:30]=[N:31][C:8](=[O:10])[C:7]3=[CH:6][N:5]=2)=[N:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 86720049Methyl 4-chloro-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylate

Product 1

HCID 178518225HCID 178518225, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.38 mmol) of methyl 4-chloro-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-5-carboxylate (example 106A) and 78.5 mg (0.75 mmol) of formamidine hydrochloride were initially charged in 1.5 ml of DMF. Subsequently, 260 μl (1.89 mmol) of triethylamine were added and conversion was effected at 80° C. overnight. After cooling, the precipitated solid was filtered off and the mother liquor was then purified by means of preparative HPLC [column: Reprosil C18, 10 μm, 250*40 mm; eluent: acetonitrile/0.05% formic acid; gradient: 10% acetonitrile→>90% acetonitrile]. Thus, 65 mg (46% of theory) of the target compound were obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid was filtered off
  3. customthe mother liquor was then purified by means of preparative HPLC [column: Reprosil C18, 10 μm, 250*40 mm; eluent: acetonitrile/0.05% formic acid; gradient: 10% acetonitrile→>90% acetonitrile]
  4. customThus, 65 mg (46% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-2d98592aba994541bd0a466f8be7be75
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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