2-Bromoethyl ethyl ether → HCID 11352891, compound

HRID 1442996Notes

Reaction equation

HRID 1442996 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([OH:27])=[CH:13][C:14]=2[O:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23](=[O:26])[CH2:24][OH:25])[N:9]=[CH:8][N:7]=1.[CH2:32]([O:34][CH2:35][CH2:36]Br)[CH3:33]>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][C:30]=1[F:31])[NH:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:27][CH2:33][CH2:32][O:34][CH2:35][CH3:36])=[CH:13][C:14]=2[O:16][CH2:17][C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23](=[O:26])[CH2:24][OH:25])[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 611412-Bromoethyl ethyl etherHCID 136344269HCID 136344269, compound

Product 1

HCID 11352891HCID 11352891, compoundYield 48%

Procedure

The procedure described in Example 17 was repeated using 4-[3-chloro-4-fluoro-anilino]-5-{[(2R)-1-glycoloylpyrrolidin-2-yl]-methoxy}-quinazolin-7-ol (70 mg) and 2-bromoethyl ethyl ether (26 μl) to give the title compound as a white solid in 48% yield; NMR Spectrum (DMSO-d6 at 373 K) 9.80 (br s, 1H), 8.40 (s, 1H), 8.15 (m, 1H), 7.65 (m, 1H), 7.33 (m, 1H), 6.80 (m, 2H), 4.60 (m, 1H), 4.50 (m, 1H), 4.30-4.10 (m, 4H), 4.0 (m, 2H), 3.75 (t, 2H), 3.55 (q, 2H), 3.48-3.37 (m, 2H), 2.10-1.85 (m, 4H), 1.15 (t, 3H); Mass spectrum MH+ 519.

Sources & evidence

ORD record
ord-2f58787d7efc4083bbdef1559656a332
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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