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Water → 4-(Benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid

HRID 2170171
Notes
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Reaction equation

HRID 2170171 reaction equation
[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]#N)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:30])(C)(C)C.CC(C)([O-])C.[K+].[OH2:37]>>[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]([OH:30])=[O:37])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 903861904-(Benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile

Product 1

HCID 903862694-(Benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acidYield 28.3%

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile (0.100 g, 0.307 mmol) dissolved in tert-butanol (15.0 mL, 157 mmol) and water (15 mL) was added potassium tert-butoxide (0.138 g, 1.23 mmol). The reaction mixture was heated in a pressure tube to 95° C. for 16 h and concentrated under reduced pressure. To the resulting residue, was added water (100 mL) and the aqueous solution was neutralized with dilute HCl to pH 7. The solid precipitated, was filtered and further purified by preparative HPLC (Condition B-74 as described in general methods) to afford 4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid (30.0 mg, 28.3%). LCMS Condition B-15: retention time 1.66 min, [M+1]=345.2. HPLC Condition B-1: retention time 14.64 min, Purity 99.30%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.71 (s, 2H), 6.29 (br s, 1H), 6.77 (d, J=2.8 Hz, 1H), 7.24-7.48 (m, 10H), 7.77 (d, J=2.8 Hz, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the resulting residue, was added water (100 mL)
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. customfurther purified by preparative HPLC (Condition B-74 as described in general methods)

Sources & evidence

ORD record
ord-4f6d35047d894907b0ce86a129ff3456
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09050345B2

Reaction notes

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