Acetic Acid → HCID 69060818, compound

HRID 1864307Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]([CH3:24])[O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=1)=[N:8][CH:9]=[N:10]2.[C:25](O)(=[O:27])[CH3:26]>>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:7]2[C:6]3[C:11](=[CH:12][CH:13]=[CH:14][C:5]=3[O:4][C@H:3]([CH3:24])[CH2:2][NH:1][C:25](=[O:27])[CH3:26])[N:10]=[CH:9][N:8]=2)=[CH:17][C:18]=1[CH3:23]

Participants

Reactant 2

HCID 176Acetic Acid

HCID 57501947HCID 57501947, compound

Product 1

HCID 69060818HCID 69060818, compoundYield 90%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using acetic acid and 4-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-methylphenol (obtained as described in Example 82, preparation of starting materials) to give N-[(2R)-2-({4-[(4-hydroxy-3-methylphenyl)amino]quinazolin-5-yl}oxy)propyl]acetamide as a ginger solid in 90% yield; NMR spectrum (DMSO-d6) 1.41 (d, 3H), 1.76 (s, 3H), 2.17 (s, 3H), 3.41 (dt, 1H), 3.62 (dt, 1H), 4.96 (m, 1H), 6.85 (d, 1H), 7.31 (d, 1H), 7.36 (m, 2H), 7.49 (d, 1H), 7.96 (t, 1H), 8.24 (t, 1H), 8.77 (s, 1H), 9.57 (s, 1H), 10.77 (s, 1H); Mass spectrum MH+ 367.

Workup

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

Sources & evidence

ORD record: ord-ff7a7d215805467e9bebc94baa160edc
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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