Ethanolamine → HCID 16118181, compound

HRID 1162274Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([NH:16][C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]=4[O:27][C@H:28]([CH3:33])[C:29](OC)=[O:30])[N:20]=[CH:19][N:18]=3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.[CH2:34]([CH2:36][NH2:37])[OH:35]>>[OH:35][CH2:34][CH2:36][NH:37][C:29](=[O:30])[C@H:28]([O:27][C:25]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:26]=1[C:17]([NH:16][C:12]1[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[N:8]=[CH:9]3)=[N:18][CH:19]=[N:20]2)[CH3:33]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 86627840HCID 86627840, compound

Product 1

HCID 16118181HCID 16118181, compoundYield 83%

Procedure

Using the same procedure as in Example 26, methyl (2R)-2-[(4-{[1-(1,3-thiazol-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-yl)oxy]propanoate (210 mg, 0.46 mmol) was reacted with ethanolamine (0.17 ml, 2.7 mmol) to give the title compound as a solid (185 mg, 83%), except that the mixture was heated at 65° C. for 2 hours. NMR Spectrum 1.65 (d, 3H), 3.21-3.25 (m, 2H), 3.42-3.46 (m, 2H), 4.75 (t, 1H), 5.23 (q, 1H), 6.04 (s, 2H), 7.02 (d, 1H), 7.37 (d, 1H), 7.66 (s, 1H), 7.73 (t, 1H), 7.77-7.79 (m, 3H) 8.21 (s, 1H), 8.48 (m, 1H), 8.54 (s, 1H), 8.57 (s, 1H), 10.75 (br s, 1H); Mass spectrum MH+ 490.

Sources & evidence

ORD record: ord-712fb7619ab5463189df19c449d54a93
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

Loading…