(R)-(-)-2-Amino-1-propanol → HCID 69061093, compound

HRID 1864286Notes

Reaction equation

HRID 1864286 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3F)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[OH:20].[NH2:21][C@H:22]([CH3:25])[CH2:23][OH:24]>>[NH2:21][C@H:22]([CH3:25])[CH2:23][O:24][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:9]([NH:8][C:6]1[CH:5]=[CH:4][C:3]([OH:20])=[C:2]([Cl:1])[CH:7]=1)=[N:10][CH:11]=[N:12]2

Participants

3

Reactant 2

HCID 80308(R)-(-)-2-Amino-1-propanolHCID 574449782-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 69061093HCID 69061093, compoundYield 100%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol (obtained as described in Example 4.5, preparation of starting materials) and (2R)-2-aminopropan-1-ol to give 4-[(5-{[(2R)-2-aminopropyl]oxy}quinazolin-4-yl)amino]-2-chlorophenol in 100% yield; NMR spectrum (DMSO-d6) 1.16 (d, 3H), 3.29-3.44 (m, 1H), 3.98 (dd, 1H), 4.22 (dd, 1H), 6.96 (d, 1H), 7.09 (d, 1H), 7.30 (d, 1H), 7.58 (dd, 1H), 7.69 (t, 1H), 8.10 (d, 1H), 8.47 (s, 1H) (4 exchangeables); Mass spectrum MH+ 344.9.

Workup

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

Sources & evidence

ORD record
ord-30167d2fda0c47dc9e4205a0240bf716
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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