L-Alaninol → HCID 69058749, compound

HRID 1864265Notes

Reaction equation

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

Participants

Reactant 2

HCID 80307L-Alaninol

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

Product 1

HCID 69058749HCID 69058749, compoundYield 54%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using (2S)-2-aminopropan-1-ol and 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol (obtained as described in Example 4.5, preparation of starting materials) to give 4-[(5-{[(2S)-2-aminopropyl]oxy}quinazolin-4-yl)amino]-2-chlorophenol in 54% yield; NMR spectrum (DMSO-d6); 1.30 (d, 3H), 3.30 (bs, 2H), 3.80 (m, 1H), 4.40 (m, 2H), 7.00 (d, 1H), 7.20 (d, 1H), 7.30 (d, 1H), 7.50 (dd, 1H), 7.70 (t, 1H), 8.00 (d, 1H), 8.45 (s, 1H); Mass spectrum MH+ 345.1.

Workup

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

Sources & evidence

ORD record: ord-6efda08cf5c94a70a307abbf103376cc
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

Loading…