Morpholine → HCID 16118034, compound

HRID 1162266Notes

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]([CH3:33])[C:30]([OH:32])=O)[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>>[CH3:33][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]([N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[O:32]

Participants

Reactant 2

HCID 8083Morpholine

HCID 68618950HCID 68618950, compound

Product 1

HCID 16118034HCID 16118034, compoundYield 34%

Procedure

Using the same procedure as in Example 44, (2S)-2-[(4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoic acid (300 mg, 0.68 mmol) was reacted with morpholine to give the title compound as a white solid (120 mg, 34%); NMR spectrum 1.58 (d, 3H), 3.67-3.58 (m, 8H), 5.77 (s, 2H), 5.88 (q, 1H), 6.95 (d, 1H), 7.29 (m, 2H), 7.35 (d, 1H), 7.75-7.67 (m, 3H), 7.83 (m, 1H), 8.15 (s, 1H), 8.52 (m, 3H), 11.12 (s, 1H); Mass spectrum MH+ 510.

Sources & evidence

ORD record: ord-a2b77987cd7c49879d79a83cc77a30ca
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

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