(2R)-1-aminopropan-2-ol → HCID 57501947, compound

HRID 1864301Notes

Reaction equation

HRID 1864301 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:5])[CH3:4].F[C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[CH:19]=1)=[N:10][CH:11]=[N:12]2>>[NH2:1][CH2:2][C@@H:3]([CH3:4])[O:5][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH3:25])[CH:19]=1)=[N:10][CH:11]=[N:12]2

Participants

3

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 574449792-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 57501947HCID 57501947, compoundYield 65%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using (R)-(−)-1-amino-propan-2-ol and 4-[(5-fluoroquinazolin-4-yl)amino]-2-methylphenol (obtained as described in Example 3, preparation of starting materials) to give 4-({5-[(1R)-2-amino-1-methylethoxy]quinazolin-4-yl}amino)-2-methylphenol as a brown solid in 65% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.16 (s, 3H), 2.96 (m, 2H), 3.30 (s, 2H), 4.96 (m, 1H), 6.77 (d, 1H), 7.14 (d, 1H), 7.25 (d, 1H), 7.44 (dd, 1H), 7.51 (d, 1H), 7.67 (t, 1H), 8.39 (s, 1H), 9.16 (s, 1H), 10.50 (s, 1H); Mass spectrum MH+ 325.

Workup

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

Sources & evidence

ORD record
ord-467353e727e244b7b52eea708c77ad07
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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