(2R)-1-aminopropan-2-ol → 4-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-chlorophenol

HRID 1864193Notes

Reaction equation

HRID 1864193 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:5])[CH3:4].[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].ClC1C=C(NC2C3C(=CC=CC=3OCCNC)N=CN=2)C=CC=1OCC1C=CC=CN=1>>[NH2:1][CH2:2][C@@H:3]([CH3:4])[O:5][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

4

Reactant 3

HCID 439938(2R)-1-aminopropan-2-olHCID 574449782-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenolHCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 575019434-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-chlorophenolYield 64%

Procedure

(R)-1-amino-2-propanol was reacted with 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol (prepared as described in Example 4-4, preparation of starting materials) using an analogous process to that described Example 1 for the preparation of N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine) to give 4-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-chlorophenol in 64% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.88-3.03 (m, 2H), 3.72-3.85 (m, 1H), 6.95 (d, 1H), 7.15 (d, 1H), 7.29 (d, 1H), 7.45-7.52 (m, 1H), 7.69, (t, 1H), 8.05 (s, 1H), 8.45 (s, 1H) Mass spectrum MH+ 345.

Sources & evidence

ORD record
ord-70ad52dfcce543e985c196164e21cfd5
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

Loading…