Triethylamine → 4-(2-Fluoro-4-(2-fluoro-5-methylbenzamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, hydrochloride salt

HRID 2117111Notes

Reaction equation

HRID 2117111 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[C:12]3=[C:13]([CH3:27])[C:14]([C:16]([NH:18][CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)=[O:17])=[CH:15][N:11]3[N:10]=[CH:9][N:8]=2)=[C:4]([F:30])[CH:3]=1.CCN(CC)CC.[F:38][C:39]1[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][C:40]=1[C:41]([Cl:43])=[O:42]>C1COCC1>[ClH:43].[F:30][C:4]1[CH:3]=[C:2]([NH:1][C:41](=[O:42])[C:40]2[CH:44]=[C:45]([CH3:48])[CH:46]=[CH:47][C:39]=2[F:38])[CH:29]=[CH:28][C:5]=1[O:6][C:7]1[C:12]2=[C:13]([CH3:27])[C:14]([C:16]([NH:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:17])=[CH:15][N:11]2[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70180482-Fluoro-5-methylbenzoyl chlorideHCID 210816664-(4-Amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

Product 1

HCID 1317262434-(2-Fluoro-4-(2-fluoro-5-methylbenzamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, hydrochloride saltYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(4-amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide (25 mg, 0.06 mmol) in 1 mL of THF were added Et3N (0.2 mL) and a solution of 2-fluoro-5-methylbenzoyl chloride (20 mg, 0.11 mmol) in 1 mL of THF at room temperature. The mixture was allowed to stir for 1 h and HPLC analysis indicated the consumption of the starting material. The reaction was quenched with MeOH. The solution was then concentrated in vacuo and the residue was purified by preparative HPLC to give the title compound (8.0 mg, 23%) as a HCl salt. 1H NMR (CD3OD) δ 8.48 (d, 1H), 7.83 (m, 3H), 7.28 (m, 3H), 7.00 (m, 1H), 2.90-4.00 (m, 12H), 2.76 (s, 3H), 2.33 (s, 3H); MS(ESI+) m/z 551.2 (M+H)+.

Workup

  1. customat room temperature
  2. customthe consumption of the starting material
  3. customThe reaction was quenched with MeOH
  4. concentrationThe solution was then concentrated in vacuo
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cbdc2f66d7c9406ab9e89d896adf355b
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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