(S)-(+)-1-Aminopropan-2-ol → HCID 69062744, compound

HRID 1864235Notes

Reaction equation

HRID 1864235 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]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[C:20]([Cl:32])[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]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[C:20]([Cl:32])[CH:19]=1)=[N:10][CH:11]=[N:12]2

Participants

3

Reactant 2

HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 57444972N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-fluoroquinazolin-4-amine

Product 1

HCID 69062744HCID 69062744, compoundYield 46%

Procedure

The procedure described in Example 1 (preparation of starting materials) was repeated using (S)-(+)-1-amino-2-propanol and 5-fluoro-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine (obtained as described in Example 1, preparation of starting materials) to give 5-[(1S)-2-amino-1-methylethoxy]-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine in 46% yield; NMR spectrum (DMSO-d6) 1.39 (d, 3H), 2.96 (m, 2H), 4.79 (m, 1H), 5.28 (s, 2H), 7.17 (d, 1H), 7.21 (d, 1H), 7.29 (d, 1H), 7.35 (m, 1H), 7.56 (d, 1H), 7.64 (dd, 1H), 7.70 (t, 1H), 7.86 (dt, 1H), 8.20 (d, 1H), 8.48 (s, 1H), 8.58 (d, 1H), 10.60 (bs, 1H); Mass Spectrum MH+ 435.

Workup

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

Sources & evidence

ORD record
ord-b565aa3a07114264b3386085382104a5
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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