Morpholine → HCID 17751626, compound

HRID 1091499Notes

Reaction equation

HRID 1091499 reaction equation
Br[CH2:2][C:3]([C:5]1[N:13]2[C:8]([C:9]([NH2:14])=[N:10][CH:11]=[N:12]2)=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]3[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=3[F:35])=[O:23])=[CH:17][CH:16]=2)[CH:6]=1)=[O:4].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C1COCC1.CCOC(C)=O.C1(C)C=CC=CC=1>[NH2:14][C:9]1[C:8]2=[C:7]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][C:26]=4[F:35])=[O:23])=[CH:17][CH:16]=3)[CH:6]=[C:5]([C:3](=[O:4])[CH2:2][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[N:13]2[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 2

HCID 8083MorpholineHCID 59232168HCID 59232168, compound

Product 1

HCID 17751626HCID 17751626, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[4-(7-bromoacetyl-4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl)phenyl]-N′-[2-fluoro-5-(trifluoromethyl)phenyl]urea (65 mg, 0.12 mmol) in 2 mL THF was treated with morpholine (53 uL, 0.59 mmol) and allowed to stir for 15 min. The reaction was then diluted with 50 mL EtOAc and 5 mL toluene & washed with sodium carbonate solution (1×). The organic layer dried with sodium sulfate and concentrated to give a yellow oil. Trituration with Et2O:hexanes (1:1) gave the title compound as a fainly yellow powder (52.4 mg, 79% Yield). 1H-NMR (DMSO-d6) 9.28 (s, 1H), 8.84 (s, 1H), 8.43 to 8.47 (m, 1H). 7.95 (s, 1H), 7.42 (d, J=8.7 Hz, 2H), 7.19 to 7.31 (m, 3H) 7.25 (d, J=8.7 Hz, 2H), 7.17 (s, 1H), 3.76 (s, 2H), 3.38 to 3.43 (m, 4H), 2.35 to 2.41 (m, 4H); MS [M+H]+=557.9; LCMS RT=2.57.

Workup

  1. washwashed with sodium carbonate solution (1×)
  2. dry with materialThe organic layer dried with sodium sulfate
  3. concentrationconcentrated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-1f8e61953ea4405e922ed57ba6b062fa
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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