Ethylene Glycol → HCID 69059589, compound

HRID 1864202Notes

Reaction equation

[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3F)[N:26]=[CH:25][N:24]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>O>[Cl:7][C:8]1[CH:9]=[C:10]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[O:3][CH2:2][CH2:1][OH:4])[N:26]=[CH:25][N:24]=2)[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Ethylene glycol (150 ml) was treated with sodium hydride (60% in oil, 3.15 g) and the exotherm controlled to about 10° C. with an ice-bath. N-[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-fluoroquinazolin-4-amine (obtained as described in Example 1, preparation of starting materials, 12 g) was added in small portions and the mixture heated at 120° C. for 1 hour. The slurry was cooled, poured into water/saturated ammonium chloride (1.5 litres) and the solid collected and dried to give 2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethanol (12.6 g, 95%); NMR spectrum (DMSO-d6) 3.89-3.98 (m, 2H), 4.33 (t, 2H), 5.27 (s, 2H), 5.37 (t, 1H), 7.13 (d, 1H), 7.23 (d, 1H), 7.31-7.38 (m, 2H), 7.57 (d, 1H), 7.68-7.75 (m, 2H), 7.83-7.90 (m, 1H), 8.26 (d, 1H), 8.54 (s, 1H), 8.58 (d, 1H), 10.41 (s, 11H); Mass spectrum MH+ 422.

Workup

customthe exotherm controlled to about 10° C. with an ice-bath
temperatureThe slurry was cooled
customthe solid collected
customdried

Sources & evidence

ORD record: ord-087e097376ca4d2e9ad4559c62878da6
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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