N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-fluoroquinazolin-4-amine → 5-{(1R)-2-[Allyl(methyl)amino]-1-methylethoxy}-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine

HRID 1864188Notes

Reaction equation

HRID 1864188 reaction equation
[CH2:1]([N:4]([CH3:9])[CH2:5][C@H:6]([OH:8])[CH3:7])[CH:2]=[CH2:3].[Cl:10][C:11]1[CH:12]=[C:13]([NH:25][C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][C:34]=3F)[N:29]=[CH:28][N:27]=2)[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.ClC1C=C(NC2C3C(=CC=CC=3OCCNC)N=CN=2)C=CC=1OCC1C=CC=CN=1>>[CH2:1]([N:4]([CH3:9])[CH2:5][C@@H:6]([CH3:7])[O:8][C:34]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:35]=1[C:26]([NH:25][C:13]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[C:11]([Cl:10])[CH:12]=1)=[N:27][CH:28]=[N:29]2)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 57444972N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-fluoroquinazolin-4-amineHCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amineHCID 86615686(2R)-1-[allyl(methyl)amino]propan-2-ol

Product 1

HCID 113523095-{(1R)-2-[Allyl(methyl)amino]-1-methylethoxy}-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amineYield 53%

Procedure

(2R)-1-[allyl(methyl)amino]propan-2-ol was reacted with N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-fluoroquinazolin-4-amine using an analogous procedure to that described in Example 1 for the preparation of N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine, to give 5-{(1R)-2-[allyl(methyl)amino]-1-methylethoxy}-N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]quinazolin-4-amine in 53% yield; NMR spectrum (DMSO-d6) 1.45 (d, 3H), 2.17 (s, 3H), 2.92-3.07 (m, 2H), 4.93 (m, 1H), 5.00 (d, 1H), 5.10 (d, 1H), 5.30 (s, 2H), 5.64 (m, 1H), 7.20-7.40 (m, 4H), 7.58 (m, 2H), 7.71 (dd, 1H), 7.85 (dd, 1H), 7.98 (m, 1H), 8.47 (s, 1H), 8.58 (d, 1H), 10.32 (bs, 1H).

Sources & evidence

ORD record
ord-a1cb89372aa34e4e875c9abe5e194512
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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