(Iodomethyl)cyclobutane → 4-Amino-6-cyclobutylmethyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

HRID 1004003Notes

Reaction equation

HRID 1004003 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:23])[CH2:17][CH2:16]2)[N:3]=1.I[CH2:31][CH:32]1[CH2:35][CH2:34][CH2:33]1>>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([O:12][CH2:31][CH:32]3[CH2:35][CH2:34][CH2:33]3)[CH:10]=2)[N:5]=[C:4]([N:15]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)=[O:23])[CH2:17][CH2:16]2)[N:3]=1

Participants

3

Reactant 2

HCID 2763052(Iodomethyl)cyclobutaneHCID 184706414-Amino-6-hydroxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

Product 1

HCID 98047774-Amino-6-cyclobutylmethyloxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline

Procedure

The title compound was prepared from 4-amino-6-hydroxy-7-methoxy-2-[4-(4-morpholinecarbonyl)-1,4-diazepan-1-yl]quinazoline and iodomethyl cyclobutane [Bailey et al J Org Chem, 60, 297-300 (1995)] following a similar procedure to that described in Example 2(b), and was obtained as a solid (14%). Rf 0.40 (0.880 aqueous ammonia:methanol:dichloromethane 1:7:92, v/v). MS m/z 471 (MH)+. Found: C, 59.35; H, 7.12; N, 17.44; C24H34N6O4 0.15CH2Cl2 0.15 H2O, requires C, 59.6 H, 7.18; N, 17.28%.

Sources & evidence

ORD record
ord-162dca260a534d0793072e3bc5b3d3ae
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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