2-(Methylamino)ethanol → HCID 16118182, compound

HRID 1162275Notes

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.[CH3:34][NH:35][CH2:36][CH2:37][OH:38]>>[OH:38][CH2:37][CH2:36][N:35]([CH3:34])[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 80162-(Methylamino)ethanol

HCID 86627840HCID 86627840, compound

Product 1

HCID 16118182HCID 16118182, compoundYield 79.9%

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 (200 mg, 0.43 mmol) was reacted with 2-(methylamino)ethanol (0.35 ml, 4.3 mmol) to give the title compound as a solid (173 mg, 79%), except that the mixture was heated at 45° C. for 24 hours and purified on an HPLC column (C18, 5 microns, 19 mm diameter, 100 mm length) of a preparative HPLC-MS system eluting with a mixture of water and acetonitrile containing 2 g/l of ammonium carbonate (gradient). NMR Spectrum (2 rotamers) 1.60-1.63 (m, 3H), 3.18 and 2.93 (s, 3H), 3.41-3.65 (m, 4H), 5.01 and 4.75 (br s, 1H), 5.81 and 5.91 (q, 1H), 6.04 (s, 2H), 7.30-7.36 (m, 2H), 7.66 (s, 1H), 7.71-7.78 (m, 3H), 8.84-8.90 (m, 1H), 8.20 (s, 1H), 8.52 (s, 1H), 8.55 and 8.58 (s, 1H), 11.12 (br s, 1H); Mass spectrum MH+ 504.

Sources & evidence

ORD record: ord-8c772947967e4289b8a78e21193ddcdc
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820683B2

Reaction notes

Loading…