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

HRID 631546Notes

Reaction equation

HRID 631546 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-2bd4d82e706e4171b449e41dfdb4b1de
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

Loading…