Diisopropylethylamine → 1-(3-Fluoro-4-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)urea

HRID 1917987Notes

Reaction equation

HRID 1917987 reaction equation
C(=O)(O)N.[F:5][C:6]1[CH:7]=[C:8]([NH:16][C:17](=[O:19])O)[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13].[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH2:33][CH2:34][O:35][CH3:36])[N:28]=[CH:27][N:26]=[C:25]2[O:37][C:38]1[CH:39]=[C:40]([CH:42]=[CH:43][CH:44]=1)[NH2:41].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C>[F:5][C:6]1[CH:7]=[C:8]([NH:16][C:17]([NH:41][C:40]2[CH:42]=[CH:43][CH:44]=[C:38]([O:37][C:25]3[C:24]4[C:29](=[CH:30][C:31]([O:32][CH2:33][CH2:34][O:35][CH3:36])=[C:22]([O:21][CH3:20])[CH:23]=4)[N:28]=[CH:27][N:26]=3)[CH:39]=2)=[O:19])[CH:9]=[CH:10][C:11]=1[C:12]([F:13])([F:14])[F:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 668758053-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)anilineHCID 671590483-Fluoro-4-(trifluoromethyl)phenylcarbamate carbamate

Product 1

HCID 582678721-(3-Fluoro-4-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)urea

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The procedure for Example 138B was used reacting 3-fluoro-4-(trifluoromethyl)phenylcarbamate carbamate as described in Example 150 (135 mg, 0.45 mmol) with amine 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)aniline from Example 117B (102 mg, 0.30 mmol). To this solution was added diisopropylethyl amine (80 μL, 0.46 mmol) and DMAP (4.0 mg, 0.03 mmol). The reaction was concentrated to dryness and triturated with dichloromethane to give 126 mg of 1-(3-fluoro-4-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-yloxy)phenyl)urea. 1H (DMSO-d6) 9.50 (s, 1H), 9.15 (s, 1H), 8.60 (s, 1H), 7.70 (m, 2H), 7.60 (s, 2H), 7.35 (m, 2H), 7.30 (m, 2H), 7.00 (m, 1H), 4.30 (m, 2H), 4.00 (s, 3H), 3.84 (m, 2H), 3.40 (s, 3H). LCMS (ESI) m/z 547 (M+H)

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customtriturated with dichloromethane

Sources & evidence

ORD record
ord-c969095da40145e5ab409666c1f0eb62
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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