Acetyl chloride → HCID 69064736, compound

HRID 1864201Notes

Reaction equation

HRID 1864201 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH2:28][CH2:29][NH:30][CH2:31][CH3:32])[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(Cl)(=[O:35])C.CCN([CH:43]([CH3:45])C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][C:25]=3[O:27][CH2:28][CH2:29][N:30]([CH2:43][CH3:45])[C:31](=[O:35])[CH3:32])[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH2:7]([O:8][CH2:9][CH3:10])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 69057020HCID 69057020, compound

Product 1

HCID 69064736HCID 69064736, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[3-Chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(ethylamino)ethoxy]quinazolin-4-amine (58 mg) in DCM (3 ml) was treated with acetyl chloride (15 mg) and DIPEA (39 mg) and stirred overnight. The solution was purified by chromatography using DCM to 10% 7N ammonia in methanol in DCM to give after trituration with diethyl ether N-{2-[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]ethyl}-N-ethylacetamide (39 mg, 61%); NMR spectrum (DMSO-d6) 1.12 (t, 3H), 1.98 (s, 3H), 3.37-3.42 (m, 2H), 3.87 (t, 2H), 4.39 (t, 2H), 5.31 (s, 2H), 7.16 (d, 1H), 7.22-7.28 (m, 1H), 7.33-7.39 (m, 2H), 7.55-7.61 (m, 2H), 7.71-7.75 (m, 1H), 7.87-7.91 (m, 1H), 7.94 (d, 1H), 8.45 (s, 1H), 8.61 (d, 1H), 9.80 (s, 1H); Mass spectrum MH+ 492.

Workup

  1. customThe solution was purified by chromatography

Sources & evidence

ORD record
ord-fe3f329ff60349a480d514b19783f7b4
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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