Hydrochloric Acid → HCID 22732281, compound

HRID 2084020Notes

Reaction equation

HRID 2084020 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH:17]3[CH2:22][CH2:21][CH2:20][N:19]([CH3:23])[CH2:18]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[NH2:24][C:25]1[CH:26]=[C:27]([NH:32][C:33]([C:35]2[CH:40]=[CH:39][N:38]=[C:37]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH:36]=2)=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31]>C(OCC)C>[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][N:19]([CH3:23])[CH2:18]1)[N:6]=[CH:5][N:4]=[C:3]2[NH:24][C:25]1[CH:26]=[C:27]([NH:32][C:33]([C:35]2[CH:40]=[CH:39][N:38]=[C:37]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH:36]=2)=[O:34])[CH:28]=[CH:29][C:30]=1[CH3:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 17904941N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamideHCID 22030702HCID 22030702, compound

Product 1

HCID 22732281HCID 22732281, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Using an analogous procedure to that described in Example 26 except that 3 equivalents of the 1M solution of hydrogen chloride in diethyl ether were used, 4-chloro-6-methoxy-7-(N-methylpiperidin-3-ylmethoxy)quinazoline was reacted with N-(3-amino-4-methylphenyl)-2-morpholinopyridine-4-carboxamide. The reaction product was purified by column chromatography on silica using an 89:10:1 mixture of methylene chloride, methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound in 34% yield; NMR: 1.12 (m, 1H), 1.52 (m, 1H), 1.65-2.05 (broad, 3H), 2.15 (s, 3H), 2.2 (s, 3H), 2.7 (m, 2H), 2.90 (m, 2H), 3.53 (m, 4H), 3.73 (m, 4H), 3.95 (s, 3H), 4.04 (d, 2H), 7.1 (m, 1H), 7.16 (s, 1H), 7.24 (m, 1H), 7.31 (m, 1H), 7.59 (m, 1H), 7.78 (m, 1H), 7.84 (s, 1H), 8.27 (m, 2H), 9.4 (s, 1H), 10.3 (s, 1H); m/s: M+H+ 598.

Workup

  1. customThe reaction product was purified by column chromatography on silica using
  2. additionan 89:10:1 mixture of methylene chloride, methanol

Sources & evidence

ORD record
ord-14fdb67c46ec45d9abab6e5ee14f140f
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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