Pyrrolidine → HCID 16117217, compound

HRID 1162226Notes

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

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 86627835HCID 86627835, compound

Product 1

HCID 16117217HCID 16117217, compoundYield 82%

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, 0.41 mmol) was reacted with pyrrolidine (0.205 ml, 2.45 mmol) to give the title compound as a light brown solid (160 mg, 82%), except that the reaction was run at 45° C. for 18 hours in the presence of 3 Å molecular sieve. NMR Spectrum 1.83 (m, 2H), 1.95 (m, 2H), 3.45 (t, 2H), 3.50 (t, 2H), 5.09 (s, 2H), 5.77 (s, 2H), 6.96 (d, 1H), 7.18 (d, 1H), 7.29 (m, 1H), 7.37 (d, 1H), 7.77-7.69 (m, 3H), 7.91 (m, 1H), 8.15 (s, 1H), 8.53 (s, 2H), 8.57 (s, 1H), 11.16 (br s, 1H); Mass spectrum MH+ 480.

Sources & evidence

ORD record: ord-2d2bed396f4e461286fafcd37d781e6d
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

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