N-Methyl-L-proline → HCID 69059787, compound

HRID 1864229Notes

Reaction equation

HRID 1864229 reaction equation
[CH3:1][N:2]1[CH2:9][CH2:8][CH2:7][C@H:3]1[C:4]([OH:6])=O.[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]=3[O:36][CH2:37][CH2:38][NH:39][CH3:40])[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>>[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]=3[O:36][CH2:37][CH2:38][N:39]([CH3:40])[C:4](=[O:6])[C@@H:3]3[CH2:7][CH2:8][CH2:9][N:2]3[CH3:1])[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

Participants

3

Reactant 2

HCID 643474N-Methyl-L-prolineHCID 69065361N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine

Product 1

HCID 69059787HCID 69059787, compoundYield 38%

Procedure

The procedure described in Example 1 was repeated using 1-methylproline and N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(methylamino)ethoxy]quinazolin-4-amine (obtained as described in Example 1, preparation of starting materials) to give the title compound in 38% yield; NMR spectrum (DMSO-d6) 1.55-1.68 (m, 3H), 1.92-2.03 (m, 2H), 2.12 (s, 2H), 3.29 (s, 6H), 3.87-4.03 (m, 2H), 4.40-4.61 (m, 2H), 5.31 (s, 2H), 7.17 (d, 1H), 7.22 (d, 1H), 7.33 (d, 1H), 7.35-7.39 (m, 1H), 7.57-7.63 (m, 2H), 7.69-7.75 (m, 1H), 7.86-7.91 (m, 1H), 8.05 (d, 1H), 8.43 (s, 1H), 8.60 (d, 1H), 9.76 (s, 1H); Mass spectrum MH+ 547.

Sources & evidence

ORD record
ord-01ee2fd29bc14c898db1eac14252976e
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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