(2R)-2-(Methylamino)propan-1-ol → HCID 69057167, compound

HRID 1864253Notes

Reaction equation

HRID 1864253 reaction equation
[CH3:1][NH:2][C@H:3]([CH3:6])[CH2:4][OH:5].[Cl:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3F)[N:18]=[CH:17][N:16]=2)[CH:11]=[CH:10][C:9]=1[OH:26]>>[Cl:7][C:8]1[CH:13]=[C:12]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[O:5][CH2:4][C@H:3]([NH:2][CH3:1])[CH3:6])[N:18]=[CH:17][N:16]=2)[CH:11]=[CH:10][C:9]=1[OH:26]

Participants

3

Reactant 2

HCID 12695787(2R)-2-(Methylamino)propan-1-olHCID 574449782-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 69057167HCID 69057167, compoundYield 100%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using (2R)-2-(methylamino)propan-1-ol (obtained as described in Becker et al., J. Chem. Soc. 1957, 858) and 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol (obtained as described in Example 4.5, preparation of starting materials) to give 2-chloro-4-[(5-{[(2R)-2-(methylamino)propyl]oxy}quinazolin-4-yl)amino]phenol in >100% yield; NMR spectrum (DMSO-d6) 1.20 (d, 3H), 2.40 (s, 3H), 3.30 (m, 1H), 4.25 (dd, 1H), 4.35 (dd, 1H), 7.00 (d, 1H), 7.10 (d, 1H), 7.30 (d, 1H), 7.60 (dd, 1H), 7.70 (t, 1H), 7.90 (d, 1H), 8.50 (s, 1H); Mass spectrum MH+ 359.1

Workup

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

Sources & evidence

ORD record
ord-5467c568cfaa4e5182e68f7286e28579
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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