Ammonia → HCID 78324270, compound

HRID 2170158Notes

Reaction equation

HRID 2170158 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]2[CH:25]=[N:26][CH:27]=[C:28]([CH:34]=2)[C:29]([O:31]CC)=O)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:35]>C(O)C>[CH2:1]([NH:8][C:9]1[C:14]2=[C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:16]=[CH:17][N:13]2[N:12]=[C:11]([C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:34]=2)[C:29]([NH2:35])=[O:31])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90386126HCID 90386126, compound

Product 1

HCID 78324270HCID 78324270, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinate (0.100 g, 0.222 mmol) in ethanol (10 mL) was purged with ammonia gas at −40° C. in a sealed tube for 15 min. The tube was sealed and the reaction mixture was stirred at ambient temperature for 14 h. The sealed tube was opened at −40° C. and allowed to rise to ambient temperature. The solvent was evaporated under reduced pressure to give a residue which was purified by preparative HPLC (Condition B-58 as described in general methods) to get 5-(4-(benzylamino)-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)nicotinamide (80.0 mg, 86.0%) as a white solid. LCMS Condition B-26: retention time 2.28 min, [M+1]=421.2. HPLC Condition B-6: retention time 7.62 min, purity 99.33%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.84 (d, J=4.0 Hz, 2H), 6.68 (t, J=4.0 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 7.25-7.32 (m, 1H), 7.34-7.41 (m, 5H), 7.45-7.48 (m, 2H), 7.52-7.54 (m, 2H), 7.67 (s, 1H), 7.93 (d, J=4.0 Hz, 1H), 8.32 (s, 1H), 8.95 (t, J=4.0 Hz, 1H), 9.11 (d, J=2.4 Hz, 1H), 9.46 (d, J=2.0 Hz, 1H).

Workup

  1. customThe tube was sealed
  2. customwas opened at −40° C.
  3. customto rise to ambient temperature
  4. customThe solvent was evaporated under reduced pressure
  5. customto give a residue which
  6. customwas purified by preparative HPLC (Condition B-58 as described in general methods)

Sources & evidence

ORD record
ord-61492c6e3f67472882f28c2866ba6ec0
Source dataset
uspto-grants-2015_06
Patent number
US09050345B2

Reaction notes

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