Pyrrolidine → HCID 16117620, compound

HRID 1162246Notes

Reaction equation

HRID 1162246 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][C@@H:29]([CH3:34])[C:30]([O:32]C)=O)[N:21]=[CH:20][N:19]=3)=[CH:14][CH:15]=2)[CH:10]=[N:9]1.[NH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH3:34][C@H: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)[C:30](=[O:32])[N:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 86627838HCID 86627838, compound

Product 1

HCID 16117620HCID 16117620, compoundYield 51.6%

Procedure

Using the same procedure as in Example 26, methyl (2S)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (250 mg, 0.55 mmol) was reacted with pyrrolidine (0.46 ml, 5.5 mmol) to give the title compound as a beige solid (140 mg, 50%), except that the mixture was heated at 55° C. for 20 hours and purified by chromatography on silica gel (eluant: 4% methanol in DCM); NMR Spectrum 1.60 (d, 3H), 1.82 (m, 2H), 1.94 (m, 2H), 3.49-3.30 (m, 3H), 3.76 (m, 1H), 5.62 (q, 1H), 5.77 (s, 2H), 6.95 (d, 1H), 7.28 (m, 2H), 7.35 (d, 1H), 7.74-7.68 (m, 3H), 7.82 (dd, 1H), 8.15 (s, 1H), 8.53 (m, 3H), 11.08 (br s, 1H); Mass spectrum MH+ 494.

Sources & evidence

ORD record
ord-05e78f957a41425bbf238fad169db35a
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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