Diisopropylethylamine → HCID 58267805, compound

HRID 1918001Notes

Reaction equation

HRID 1918001 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:22])OC2C=CC=CC=2)[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10].[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH2:36][CH2:37][O:38][CH3:39])[N:31]=[CH:30][N:29]=[C:28]2[S:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][CH:47]=1)[NH2:44].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]([NH:44][C:43]2[CH:45]=[CH:46][CH:47]=[C:41]([S:40][C:28]3[C:27]4[C:32](=[CH:33][C:34]([O:35][CH2:36][CH2:37][O:38][CH3:39])=[C:25]([O:24][CH3:23])[CH:26]=4)[N:31]=[CH:30][N:29]=3)[CH:42]=2)=[O:22])[CH:6]=[CH:7][C:8]=1[C:9]([F:10])([F:11])[F:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 66876321Phenyl 3-methoxy-4-(trifluoromethyl)phenylcarbamateHCID 668767643-(6-Methoxy-7-(2-methoxyethoxy)quinazolin-4-ylthio)aniline

Product 1

HCID 58267805HCID 58267805, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The procedure for Example 138B was used to react phenyl 3-methoxy-4-(trifluoromethyl)phenylcarbamate described in Example 190B (144 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 purified by silica gel chromatography eluting with ethyl acetate/dichloromethane 0-50% over 75 minutes. The main peak collected and concentrated, then triturated with dichloromethane to give a solid weighing 43 mg. 1H (DMSO-d6) 9.19 (s, 1H), 9.04 (s, 1H), 8.70 (s, 1H), 7.84 (s, 1H), 7.6-7.40 (m, 4H), 7.35 (m, 2H), 7.25 (m, 1H), 7.00 (m, 1H), 4.34 (m, 2H), 4.00 (s, 3H), 3.84 (s, 3H), 3.78 (m, 2H). LCMS (ESI) m/z 575 (M+H)

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. custompurified by silica gel chromatography
  3. washeluting with ethyl acetate/dichloromethane 0-50% over 75 minutes
  4. customThe main peak collected
  5. concentrationconcentrated
  6. customtriturated with dichloromethane
  7. customto give a solid

Sources & evidence

ORD record
ord-f9b9955cc1724c79aa8e8ed9d0cf4cdb
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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