Diisopropylethylamine → HCID 44242858, compound

HRID 1917959Notes

Reaction equation

HRID 1917959 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[C:10]([NH:18][C:19](=[O:27])OC3C=CC=CC=3)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=2)[CH2:3][CH2:2]1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[N:36]=[CH:35][N:34]=[C:33]2[S:42][C:43]1[CH:44]=[C:45]([CH:47]=[CH:48][CH:49]=1)[NH2:46].C(N(C(C)C)CC)(C)C>CN(C1C=CN=CC=1)C>[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[N:36]=[CH:35][N:34]=[C:33]2[S:42][C:43]1[CH:44]=[C:45]([NH:46][C:19]([NH:18][C:10]2[CH:11]=[C:12]([C:14]([F:15])([F:17])[F:16])[CH:13]=[C:8]([CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:9]=2)=[O:27])[CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 569536273-(6,7-Dimethoxyquinazolin-4-ylthio)anilineHCID 66876404HCID 66876404, compound

Product 1

HCID 44242858HCID 44242858, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The procedure described in Example 138B was used to react phenyl 3-(morpholinomethyl)-5-(trifluoromethyl)phenylcarbamate described in example 151A (140 mg, 0.37 mmol) with 3-(6,7-dimethoxyquinazolin-4-ylthio)aniline from Example 115B (77 mg, 0.25 mmol). To this solution was added diisopropylethyl amine (64 μL, 0.37 mmol) and DMAP (3.0 mg, 0.03 mmol). The reaction was concentrated to dryness and triturated with methanol to give 47 mg. 1H NMR (300 MHz, DMSO-d6) δ 9.15 (s, 1H), 8.98 (s, 1H), 8.70 (s, 1H), 7.88 (d, 2H), 7.55 (m, 2H), 7.44 (m, 1H), 7.35 (s, 2H), 7.25 (m, 2H), 4.00 (s, 6H), 3.58 (s, 4H), 3.34 (s, 2H), 2.39 (s, 4H). LCMS (ESI) m/z 600 (M+H)

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. customtriturated with methanol
  3. customto give 47 mg

Sources & evidence

ORD record
ord-ad1e55ab344948a898c183eff894aaff
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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