4-Fluorophenylboronic acid → HCID 22707080, compound

HRID 353044Notes

Reaction equation

HRID 353044 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]=2I)[N:5]=[C:4]([N:17]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[CH2:19][CH2:18]2)[N:3]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1>CCOC(C)=O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]=2[C:36]2[CH:37]=[CH:38][C:33]([F:32])=[CH:34][CH:35]=2)[N:5]=[C:4]([N:17]2[CH2:23][CH2:22][CH2:21][N:20]([C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[CH2:19][CH2:18]2)[N:3]=1

Participants

4

Reactant 2

HCID 2856454-Fluorophenylboronic acidHCID 227070704-Amino-6,7-dimethoxy-5-iodo-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

Product 1

HCID 22707080HCID 22707080, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

This was prepared by the method of Example 1(a) from the product of step (c) (1.2/1 mixture, w/w) and 4-fluorophenylboronic acid. The crude product was purified on silica gel, eluting initially with hexane/EtOAc (4/1, v/v) followed by EtOAc. The title compound (63% based on the compound of step (c)) was obtained as a white foam. Rf 0.18 (EtOAc). MS m/z 511 (MH+). 1H NMR (CDCl3) δ: 2.00 (2H, m), 3.14 (4H, m), 3.35 (2H, m), 3.48 (3H, s), 3.55 (2H, m), 3.66 (4H, m), 3.84 (2H, m), 3.94 (2H, m), 3.97 (3H, s), 4.52 (2H, bs), 6.90 (1H, bs), 7.16 (2H, m), 7.32 (2H, m). Found: C,60.91; H,6.32; N,15.73; C26H31N6O4F 0.2.EtOAc requires C,60.90; H,6.17; N,15.91%.

Workup

  1. customThe crude product was purified on silica gel
  2. washeluting initially with hexane/EtOAc (4/1
  3. customwas obtained as a white foam

Sources & evidence

ORD record
ord-3d0b2f554a5a4a7e9f68a50a63ad1d58
Source dataset
uspto-grants-2004_06
Patent number
US06750214B2

Reaction notes

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