Morpholine → HCID 16117218, compound

HRID 1162227Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]=4[O:28][CH2:29][C:30](OC)=[O:31])[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>>[N:34]1([C:30](=[O:31])[CH2:29][O:28][C:26]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:27]=2[C:18]([NH:17][C:13]2[CH:12]=[C:11]4[C:16](=[CH:15][CH:14]=2)[N:8]([CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:9]=[CH:10]4)=[N:19][CH:20]=[N:21]3)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

Reactant 2

HCID 8083Morpholine

HCID 86627835HCID 86627835, compound

Product 1

HCID 16117218HCID 16117218, compoundYield 59%

Procedure

Using the same procedure as in Example 5, methyl [(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]acetate (180 mg, 0.40 mmol) was reacted with morpholine (0.346 ml, 3.96 mmol) to give the title compound as a solid (115 mg, 59%), except that the reaction was run at 60° C. for 32 hours in the presence of 3 Å molecular sieve. NMR Spectrum 3.68-3.52 (m, 8H), 5.20 (s, 2H), 5.77 (s, 2H), 6.96 (d, 1H), 7.23 (d, 1H), 7.30 (m, 1H), 7.37 (d, 1H), 7.77-7.68 (m, 3H), 7.90 (m, 1H), 8.15 (s, 1H), 8.53 (s, 2H), 8.56 (s, 1H), 11.18 (br s, 1H); Mass spectrum MH+ 496.

Sources & evidence

ORD record: ord-7196aea2bdb64ce2be2fccd2d144ecec
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

Loading…