Ethanolamine → HCID 69063573, compound

HRID 1864282Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3F)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:20].[CH2:21]([CH2:23][NH2:24])[OH:22]>>[NH2:24][CH2:23][CH2:21][O:22][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([OH:20])=[C:2]([Cl:1])[CH:7]=1)=[N:10][CH:11]=[N:12]2

Participants

Reactant 2

HCID 700Ethanolamine

HCID 574449782-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 69063573HCID 69063573, compoundYield 84%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol (obtained as described in Example 4.5, preparation of starting materials) and ethanolamine to give 4-{[5-(2-aminoethoxy)quinazolin-4-yl]amino}-2-chlorophenol in 84% yield. NMR spectrum (DMSO-d6) 3.12 (t, 2H), 4.27 (t, 2H), 6.96 (d, 1H), 7.11 (d, 1H), 7.31 (d, 1H), 7.53 (dd, 1H), 8.08 (d, 1H), 8.47 (s, 1H); Mass spectrum MH+ 331.0.

Workup

customThe procedure described in Example 3 (preparation of starting materials)

Sources & evidence

ORD record: ord-6586d5884c544dbebdb4e42b618e6623
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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