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

HRID 1917999Notes

Reaction equation

HRID 1917999 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:12][C:13](=[O:15])[O-])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH2:29][CH2:30][O:31][CH3:32])[N:24]=[CH:23][N:22]=[C:21]2[S:33][C:34]1[CH:35]=[C:36]([CH:38]=[CH:39][CH:40]=1)[NH2:37].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]([NH:37][C:36]2[CH:38]=[CH:39][CH:40]=[C:34]([S:33][C:21]3[C:20]4[C:25](=[CH:26][C:27]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[C:18]([O:17][CH3:16])[CH:19]=4)[N:24]=[CH:23][N:22]=3)[CH:35]=2)=[O:15])[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 668767643-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)anilineHCID 866535203-Fluoro-4-(trifluoromethyl)phenylcarbamate

Product 1

HCID 582679141-(3-Fluoro-4-(trifluoromethyl)phenyl)-3-(3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)phenyl)urea

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The procedure for Example 138B was used to react 3-fluoro-4-(trifluoromethyl)phenylcarbamate as described in Example 150 (138 mg, 0.46 mmol) with 3-(6-methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)aniline described in Example 231A (110 mg, 0.31 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 122 mg. 1H (DMSO-d6) 9.43 (s, 1H), 9.15 (s, 1H), 8.70 (s, 1H), 7.84 (s, 1H), 7.70 (m, 2H), 7.60 (m, 1H), 7.50 (m, 1H), 7.40 (m, 4H), 4.34 (m, 2H), 4.00 (s, 3H), 3.78 (m, 2H), 3.38 (m, 3H). LCMS (ESI) m/z 563 (M+H)

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customtriturated with dichloromethane
  3. customto give 122 mg

Sources & evidence

ORD record
ord-bb89a7bf58f34edf86b5f868a4893de7
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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